Category: 3400-55-3

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: 2-Bromopriopionaldehydediethylacetal(SMILESS: CC(Br)C(OCC)OCC,cas:3400-55-3) is researched.Safety of 1-(Bromomethyl)-4-iodobenzene. The article 《Vinylindenes and some heteroanalogs in the Diels-Alder reaction. VI. Vinylbenzo[b]thiophenes and ethenetetracarbonitrile》 in relation to this compound, is published in Australian Journal of Chemistry. Let’s take a look at the latest research on this compound (cas:3400-55-3).

3-Vinylbenzo[b]thiophene and 3 simple homologs give normal Diels-Alder adducts, e.g. I, with ethenetetracarbonitrile, whereas the 3-methyl-2-vinyl- and 2-methyl-3-(1-propenyl) derivatives give cyclobutanes, e.g. II. 2-Methyl-3-vinylbenzo[b]thiophene and ethenetetracarbonitrile give an adduct resulting from reaction of a tautomeric form of the diene, but a naphthalene analog and a phenanthrene analog of this substituted benzothiophene give normal adducts.

In some applications, this compound(3400-55-3)Computed Properties of C7H15BrO2 is unique.If you want to know more details about this compound, you can contact with the author or consult more relevant literature.

Reference:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics

In general, if the atoms that make up the ring contain heteroatoms, such rings become heterocycles, and organic compounds containing heterocycles are called heterocyclic compounds. An article called New organic sulfur vesicants. II. Analogues of 2,2′-dichlorodiethyl sulfide and 2,2′-di(2-chloroethylthio)diethyl ether, published in 1948, which mentions a compound: 3400-55-3, Name is 2-Bromopriopionaldehydediethylacetal, Molecular C7H15BrO2, HPLC of Formula: 3400-55-3.

MeCH.CH2.O (680 g.), introduced at the rate of 0.7 cc./min., and H2S (throughput 45 l./h.) at 60° give 948 g. of product which yields 488 g. 2-hydroxy-1-propanethiol, b8 44.5-5°, n18D 1.4850, and 390 g. 2,2′-dihydroxydipropyl sulfide (I), b4 125°. ClCH2CHMeOH (b. 126-8°) and Na2S in EtOH, refluxed 10 min., give I. I (50 g.) in 200 cc. CHCl3, treated dropwise with 62 cc. SOCl2 and refluxed 30 min., gives bis(2-chloropropyl) sulfide, b10 105°, m. -40°. EtCHO (58 g.) in 300 cc. AcOEt at -5°, treated dropwise (3 h.) with 45 g. Br in 100 cc. AcOEt, and the mixture poured into 500 cc. absolute EtOH and kept 18 h. at room temperature, give CHMeBrCH(OEt)2, b13 67°; reaction with HSC2H4OH in EtONa-EtOH (refluxing 25 h.) gives α-(2-hydroxyethylmercapto)propionaldehyde di-Et acetal, b0.5 87°; hydrolysis of 40 g. with 200 cc. 3% HCl (24 h.) gives α-(2-hydroxyethylmercapto)propionaldehyde, an oil, reduction of which with (iso-PrO)3Al gives 2-hydroxyethyl 2-hydroxyisopropyl sulfide, b5 136-7°; SOCl2 yields 2-chloroethyl 2-chloroisopropyl sulfide, b7 88°, b12 105°, m. -24.5° (sulfilimine, m. 132°). S(CH2CH2SCH2CH2OH)2 (II) (C.A. 16, 409) and SOCl2 in CHCl3 (refluxed 30 min.) give 2,2′-bis(2-chloroethylmercapto)diethyl sulfide (III), m. 73-5° (chloroplatinate, mustard color, m. 136°; piperidide picrate, m. 180° (decomposition)). The Cl atom of III is removed by AgNO3 in boiling EtOH in 5 min. and by boiling H2O in 45 min. The following ethers were prepared from III and the appropriate phenol in EtOH-EtONa: diphenoxy, m. 59°; di-2-naphthoxy, m. 122°; bis(sym-tribromophenoxy), m. 107°; dieugenoxy, m. 86°; bis(phenylmercapto), m. 92-4°. III and NaI in MeOH, refluxed 10 min., give the bis(2-iodoethyl) analog, m. 102-3°; bis(2-thiocyanatoethyl) analog, m. 52°; the bis(2-cyanoethyl) analog could not be prepared, the reaction yielding (NCCH2CH2)2S and dithiane. II and PBr3 in CHCl3, refluxed 2 h., give the bis(2-bromoethyl) analog, b3.5 158-63.5° [bis(1-naphthylurethane), m. 150-2°]. (ClCH2CH2)2S2 b5 132-4° [bis(sym-tribromophenoxy) analog, m. 76°; dieugenoxy analog, m. 97°]. III in AcOH, treated with 6 mols. 30% H2O2 (1 h.) gives 2,2′-bis(2-chloroethylsulfonyl)diethyl sulfone, m. 174.5°; 2,2′-bis(2-hydroxyethylmercapto)diethyl sulfoxide, m. 57°; the sulfone m. 85-6°; the disulfide m. 79-81°; 2,2′-bis(2-chloroethylmercapto)diethyl sulfoxide, m. 63°; the sulfone m. 107-9°; 2,2′-bis(2-hydroxypropylmercapto)diethyl sulfide, m. 59°; di-2-Cl analog, m. 43.5°; 2,3-bis(2-hydroxyethylmercapto)-1,4-dioxane, oily [bis(1-naphthylurethane), m. 152°]; 2,3-bis(2-chloroethylmercapto)-1,4,-dioxane, b15 138-41°. 2-Hydroxyethyl 2-hydroxypropyl sulfide, b8 154°; 2-chloroethyl 2-chloropropyl sulfide, b4 88°, m. -23°. 2,2′-Bis(2-hydroxypropylmercapto)diethyl ether, b5 217-18°; di-2-Cl analog, b0.02 95-8°. 2,2′-Bis(2-hydroxyethymercapto)dipropyl sulfide, b1.5 240°; di-2-Cl analog. 2,2′-Bis(2-hydroxypropylmercapto)dipropyl sulfide, b0.5 210°; di-2-Cl analog, b0.02 108-9° (slight decomposition). If mustard gas is assigned an empirical vesicant power of 100, these compounds show values of 10 to 50.

In addition to the literature in the link below, there is a lot of literature about this compound(2-Bromopriopionaldehydediethylacetal)HPLC of Formula: 3400-55-3, illustrating the importance and wide applicability of this compound(3400-55-3).

Reference:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics

Reference of 2-Bromopriopionaldehydediethylacetal. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: 2-Bromopriopionaldehydediethylacetal, is researched, Molecular C7H15BrO2, CAS is 3400-55-3, about Structural alterations that differentially affect the mutagenic and antitrichomonal activities of 5-nitroimidazoles. Author is Walsh, John S.; Wang, Regina; Bagan, Edward; Wang, C. C.; Wislocki, Peter; Miwa, Gerald T..

Two approaches have been used to develop nonmutagenic 5-nitroimidazoles, both of which are based on knowledge of the likely mechanisms by which this class of compounds cause mutagenicity. The first approach involves incorporating readily oxidizable gallate derivatives into the mol. In one case, a very weakly mutagenic active antitrichomonal agent was obtained. The second approach involved incorporating a substituent at the C-4 position of the ring. This generally resulted in a large reduction in mutagenicity and a lowering of antitrichomonal activity in vitro. In certain cases, however, mutagenicity was dramatically reduced while moderate antitrichomonal activity was retained. For example, 1,2-dimethyl-4-(2-hydroxyethyl)-5-nitroimidazole (I) showed good antitrichomonal activity in vitro (ED50 = 2 μg/kg) while possessing only 4% of the mutagenicity of metronidazole.

In addition to the literature in the link below, there is a lot of literature about this compound(2-Bromopriopionaldehydediethylacetal)Reference of 2-Bromopriopionaldehydediethylacetal, illustrating the importance and wide applicability of this compound(3400-55-3).

Reference:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: 2-Bromopriopionaldehydediethylacetal, is researched, Molecular C7H15BrO2, CAS is 3400-55-3, about Convenient method for the synthesis of 2-(1-alkenyl)-2-cyclopentenones, the main research direction is cyclopentenone alkenyl; bromo acetal addition enol; silyl enol ether addition.Safety of 2-Bromopriopionaldehydediethylacetal.

Treatment of α-bromo acetals, BrCRR1CR2(OR3)2 [R = H, Me; R1 = H, Me, Et, Bu; R2 = H; or R1R2 = (CH2)4; R3 = Me, Et], with TiCl4 and then with silyl enol ether I (in CH2Cl2 dropwise at -78° under argon) gave β-alkoxy-γ-bromo ketones which were heated first in PhMe-P-MeC6H4SO3H and then DMF-Et3V to give the title cyclopentenones II. Brominated derivatives were also formed in some cases by addition of HBr (eliminated in the reactions) to the double bonds of II.

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Reference:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 2-Bromopriopionaldehydediethylacetal( cas:3400-55-3 ) is researched.Application of 3400-55-3.Migulin, Vasily A.; Krayushkin, Michael M.; Barachevsky, Valery A.; Kobeleva, Olga I.; Novikov, Valentin V.; Lyssenko, Konstantin A. published the article 《Synthesis and studies of symmetric dibenzothienylcyclopentenes》 about this compound( cas:3400-55-3 ) in Tetrahedron. Keywords: sym dibenzothienylcyclopentene photochromism crystal structure DFT. Let’s learn more about this compound (cas:3400-55-3).

Various sym. 5,5′-substituted dibenzo[b]thienylcyclopentenes were synthesized from the corresponding dibromide with a formation of new C-C, C-N, C-O, C-Si, and C-I bonds. The influence of the introduced substituent on the photochromic properties of the obtained compounds was systematically researched in both solution and solid state. The ratio of antiparallel and parallel conformers in solution was determined by NMR spectroscopy. Only one compound of the series-5,5′-diphenoxy-substituted-has displayed photochromism in the single crystal. High resolution x-ray diffraction showed that intermol. S···π and S···H contacts kept two benzothiophene rings together in the mol., hence decreasing the distance between the two reactive centers responsible for the photocyclization reaction. DFT calculations of the isolated mols. appeared to be in good agreement with the obtained x-ray diffraction data, and therefore could also essentially assist a researcher in the design of photochromic mols.

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Reference:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Synthesis of 4-Acylchromene via Highly Chemoselective Iodine-Catalyzed Cyclization of Alkynylarylether Dimethylacetals》. Authors are Rodphon, Warabhorn; Thongsornkleeb, Charnsak; Tummatorn, Jumreang; Ruchirawat, Somsak.The article about the compound:2-Bromopriopionaldehydediethylacetalcas:3400-55-3,SMILESS:CC(Br)C(OCC)OCC).Electric Literature of C7H15BrO2. Through the article, more information about this compound (cas:3400-55-3) is conveyed.

A metal-free method for the synthesis of 4-acylchromene derivatives I [R1 = Ph, 4-MeC6H4, 4-FC6H4, etc.; R2 = H, 6-Cl, 7-OMe, etc.] and II [R3 = H, Me, CH2Cl; R4 = H, Me] via highly chemoselective iodine-catalyzed cyclization of alkynylarylether dimethylacetals was reported. A combination of acetone and catalytic I2 lead to selective activation of acetal in alkynylarylether dimethylacetal substrates while alkyne moiety remained intact. Also this method was a safe, cost-effective, convenient and environmentally-friendly.

Here is just a brief introduction to this compound(3400-55-3)Electric Literature of C7H15BrO2, more information about the compound(2-Bromopriopionaldehydediethylacetal) is in the article, you can click the link below.

Reference:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Synthesis of 4-Acylchromene via Highly Chemoselective Iodine-Catalyzed Cyclization of Alkynylarylether Dimethylacetals》. Authors are Rodphon, Warabhorn; Thongsornkleeb, Charnsak; Tummatorn, Jumreang; Ruchirawat, Somsak.The article about the compound:2-Bromopriopionaldehydediethylacetalcas:3400-55-3,SMILESS:CC(Br)C(OCC)OCC).Electric Literature of C7H15BrO2. Through the article, more information about this compound (cas:3400-55-3) is conveyed.

A metal-free method for the synthesis of 4-acylchromene derivatives I [R1 = Ph, 4-MeC6H4, 4-FC6H4, etc.; R2 = H, 6-Cl, 7-OMe, etc.] and II [R3 = H, Me, CH2Cl; R4 = H, Me] via highly chemoselective iodine-catalyzed cyclization of alkynylarylether dimethylacetals was reported. A combination of acetone and catalytic I2 lead to selective activation of acetal in alkynylarylether dimethylacetal substrates while alkyne moiety remained intact. Also this method was a safe, cost-effective, convenient and environmentally-friendly.

Here is just a brief introduction to this compound(3400-55-3)Electric Literature of C7H15BrO2, more information about the compound(2-Bromopriopionaldehydediethylacetal) is in the article, you can click the link below.

Reference:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Ketene acetals. XXXIII. The addition of halogens and cyanogen compounds to methylketene diethyl acetal》. Authors are McElvain, S. M.; McLeish, Wm. L..The article about the compound:2-Bromopriopionaldehydediethylacetalcas:3400-55-3,SMILESS:CC(Br)C(OCC)OCC).Synthetic Route of C7H15BrO2. Through the article, more information about this compound (cas:3400-55-3) is conveyed.

cf. C.A. 49, 14687i. Salts of the type [MeCHXC(OEt)2]Xn-1 (n = 4 when X = iodine; n = 0 and 2 when X = Br) have been isolated and shown to be the intermediates through which certain dimeric products are formed when these halogens react with MeCH:C(OEt)2 (I). (CN)2 did not react with I, but both BrCN and ICN add readily to give only MeCHXC(OEt)2CN in high yields. HCN reacted exothermically with I to yield the monomeric and dimeric addition products, EtC(OEt)2CN (II) and EtC(OEt)2CHMeC(OEt)2CN (III). I (16.0 g. ) in 300 cc. Et2O at 25 ° treated with stirring with 14.4 g. iodine during 1.75 h., the solvent and EtI distilled off at 9 mm., and the residue distilled gave 3.5 g. MeCHICO2Et (IV); 2.4 g. EtC(OEt)2CMe:C(OEt)2 (V), b0.25 47°, nD25 1.4305 (V first added and then substituted Br and slowly gave a green color with FeCl3); and 14.5 g. MeCHIC(OEt)2CHMeCO2Et (VI), b0.25 92°, nD25 1.4782 (VI when treated with Br or on standing liberated iodine). VI ( 13.2 g.) heated 15 min. at 210° gave 6.86 g. EtI-EtOH azeotrope; the dark brown residue yielded 0.95 g. Et α,γ-dimethyltetronate, b. 153-68°, nD25 1.4731, which hydrolyzed gave the free acid, m. 121.5-2.5°. V (6.85 g.) and 1.52 g. H2O heated 0.5 h. with stirring at 85-95°, and the solution dried and distilled gave 2.65 g. EtCOCHMeCO2Et, which yielded a pyrazolone, m. 108-10°. I (16.5 g.) added dropwise during 1 h. to 25.2 g. iodine in 500 cc. Et2O at 25° and the solution distilled gave 18.5 g. IV and 5.3 g. VI. Iodine (2.17 g.) in 28 cc. Et2O added during 1 h. to 11.1 g. I in 117 cc. Et2O at 0° and the mixture distilled gave 8.0 g. unchanged I, 1.75 g. V, and 1.05 g. VI. Iodine (61.0 g.) in 450 cc. Et2O treated with stirring at 0-5° with 31.2 g. I during 40 min., the light yellow, supernatant liquid forced through a filter stick, the remaining solid treated with 200 cc. cold Et2O and 25 cc. cold H2O, the mixture titrated with aqueous Na2S2O3 until colorless (0.118 mol iodine was present), the aqueous layer titrated with base (0.058 mol acid present), and the Et2O layer distilled gave 11.8 g. IV; these titrations showed the salt to be [MeCHIC(OEt)2]I5. Iodine (119.8 g.) in 800 cc. Et2O treated at about -3° with 20.4 g. I during 15 min., and the heavy brown precipitate worked up and titrated in the usual manner, and finally treated with H2O gave 22.5 g. IV. Iodine (49.6 g.) and 25.4 g. mixed with 100 cc. cold Et2O, the Et2O suspension treated with 27.7 g. I, and the mixture worked up gave 6.6 g. IV, 7.0 g. V, 20.4 g. VI, and 3.5 g. unchanged I. I (10.2 g.) in 100 cc. Et2O treated with 21.3 g. iodine in 200 cc. Et2O at 0° during 3 h., and the orange solution distilled gave 18.1 g. Me2CHICO2Et, b12 64°, nD25 1.5010. I (21.0 g.) in 100 cc. CCl4 added during 35 min. with stirring at -5° to 98.5 g. Br in 200 cc. CCl4, the solvent removed through a filter stick, the residual heavy, granular, red solid shaken with 20 cc. cold H2O, the mixture treated with 100 g. KI in H2O and titrated with Na2S2O3 (0.303 mol Br present), and the organic layer extracted and distilled gave 12.2 g. MeCHBrCO2Et (VII); the CCl4 filtrate (from the red solid) shaken with 76 g. KI in H2O, decolorized with 0.345 equivalent Na2S2O3, and distilled gave 8.8 g. VII. I (10.6 g.) in 40 cc. CCl4 added during 1 h. at 0° to 12.5 g. Br in 60 cc. CCl4 gave 2.1 g. orange solid which contained 58.3% Br (dried at 0.1 mm. and 0°). I (2.6 g.) added to 6.4 g. Br in 8 cc. CCl4 at -25 to -30° gave 4.1 g. red solid containing 69.5% Br. I (30.1 g.) added at 0° during 40 min. to 20.2 g. ICl in 100 cc. CCl4 and the mixture distilled twice gave 5.4 g. MeCHClCO2Et, 9.1 g. IV, 7.9 g. V, and 5.7 g. VI. (CN)2 bubbled through 18.3 g. I at 100° with stirring during 3 h. and distilled gave only 16.0 g. unchanged I. I (51.1 g.) added slowly with stirring during 25 min. to 47.1 g. BrCN in 70 cc. Et2O and distilled gave 90.4 g. MeCHBrC(OEt)2CN (VIII), b16 108°, nD25 1.4463, d25 1.2611. I (19.6 g.) in 150 cc. Et2O treated with stirring with 18.0 g. BrCN in 50 cc. Et2O an distilled gave 28.9 g. VIII. VIII (6.00 g.) shaken 8 h. with 4.32 g. AgNO3 in 150 cc. Et2O, and the precipitate filtered, washed with Et2O, and dried gave 3.5 g. AgCN; the aqueous layer contained 0.181 mol acid; the Et2O washings distilled gave 3.5 g. VII, b14 54°, nD25 1.4427. VIII (10 g.) refluxed (210°) 5.5 h., and the HCN evolved passed into aqueous AgNO3 gave 1.2 g. AgCN; the residue distilled gave 23% impure VII, nD25 1.4414-1.4433. I (9.7 g.) added dropwise to 11.4 g. ICN in 50 cc. Et2O and distilled gave 18.5 g. MeCHIC(OEt)2CN, b0.15 84-9°, nD25 1.4798. I (11.8 g.) added with stirring to 2.45 g. HCN at -10° and distilled gave 12.2 g. II, b10 62-3°, nD25 1.4040, d25 0.9113, MRD 42.19; and 0.5 g. III, b0.25 70°, nD25 1.4330, 0.9641, MRD 77.53. I (17.1 g.) treated with cooling with 3.9 g. liquid HCN during 20 min. and the mixture kept 1.5 days at 25° and distilled gave 14.6 g. II and 4.7 g. XIII.

Compound(3400-55-3)Synthetic Route of C7H15BrO2 received a lot of attention, and I have introduced some compounds in other articles, similar to this compound(2-Bromopriopionaldehydediethylacetal), if you are interested, you can check out my other related articles.

Reference:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Ketene acetals. XXXIII. The addition of halogens and cyanogen compounds to methylketene diethyl acetal》. Authors are McElvain, S. M.; McLeish, Wm. L..The article about the compound:2-Bromopriopionaldehydediethylacetalcas:3400-55-3,SMILESS:CC(Br)C(OCC)OCC).Synthetic Route of C7H15BrO2. Through the article, more information about this compound (cas:3400-55-3) is conveyed.

cf. C.A. 49, 14687i. Salts of the type [MeCHXC(OEt)2]Xn-1 (n = 4 when X = iodine; n = 0 and 2 when X = Br) have been isolated and shown to be the intermediates through which certain dimeric products are formed when these halogens react with MeCH:C(OEt)2 (I). (CN)2 did not react with I, but both BrCN and ICN add readily to give only MeCHXC(OEt)2CN in high yields. HCN reacted exothermically with I to yield the monomeric and dimeric addition products, EtC(OEt)2CN (II) and EtC(OEt)2CHMeC(OEt)2CN (III). I (16.0 g. ) in 300 cc. Et2O at 25 ° treated with stirring with 14.4 g. iodine during 1.75 h., the solvent and EtI distilled off at 9 mm., and the residue distilled gave 3.5 g. MeCHICO2Et (IV); 2.4 g. EtC(OEt)2CMe:C(OEt)2 (V), b0.25 47°, nD25 1.4305 (V first added and then substituted Br and slowly gave a green color with FeCl3); and 14.5 g. MeCHIC(OEt)2CHMeCO2Et (VI), b0.25 92°, nD25 1.4782 (VI when treated with Br or on standing liberated iodine). VI ( 13.2 g.) heated 15 min. at 210° gave 6.86 g. EtI-EtOH azeotrope; the dark brown residue yielded 0.95 g. Et α,γ-dimethyltetronate, b. 153-68°, nD25 1.4731, which hydrolyzed gave the free acid, m. 121.5-2.5°. V (6.85 g.) and 1.52 g. H2O heated 0.5 h. with stirring at 85-95°, and the solution dried and distilled gave 2.65 g. EtCOCHMeCO2Et, which yielded a pyrazolone, m. 108-10°. I (16.5 g.) added dropwise during 1 h. to 25.2 g. iodine in 500 cc. Et2O at 25° and the solution distilled gave 18.5 g. IV and 5.3 g. VI. Iodine (2.17 g.) in 28 cc. Et2O added during 1 h. to 11.1 g. I in 117 cc. Et2O at 0° and the mixture distilled gave 8.0 g. unchanged I, 1.75 g. V, and 1.05 g. VI. Iodine (61.0 g.) in 450 cc. Et2O treated with stirring at 0-5° with 31.2 g. I during 40 min., the light yellow, supernatant liquid forced through a filter stick, the remaining solid treated with 200 cc. cold Et2O and 25 cc. cold H2O, the mixture titrated with aqueous Na2S2O3 until colorless (0.118 mol iodine was present), the aqueous layer titrated with base (0.058 mol acid present), and the Et2O layer distilled gave 11.8 g. IV; these titrations showed the salt to be [MeCHIC(OEt)2]I5. Iodine (119.8 g.) in 800 cc. Et2O treated at about -3° with 20.4 g. I during 15 min., and the heavy brown precipitate worked up and titrated in the usual manner, and finally treated with H2O gave 22.5 g. IV. Iodine (49.6 g.) and 25.4 g. mixed with 100 cc. cold Et2O, the Et2O suspension treated with 27.7 g. I, and the mixture worked up gave 6.6 g. IV, 7.0 g. V, 20.4 g. VI, and 3.5 g. unchanged I. I (10.2 g.) in 100 cc. Et2O treated with 21.3 g. iodine in 200 cc. Et2O at 0° during 3 h., and the orange solution distilled gave 18.1 g. Me2CHICO2Et, b12 64°, nD25 1.5010. I (21.0 g.) in 100 cc. CCl4 added during 35 min. with stirring at -5° to 98.5 g. Br in 200 cc. CCl4, the solvent removed through a filter stick, the residual heavy, granular, red solid shaken with 20 cc. cold H2O, the mixture treated with 100 g. KI in H2O and titrated with Na2S2O3 (0.303 mol Br present), and the organic layer extracted and distilled gave 12.2 g. MeCHBrCO2Et (VII); the CCl4 filtrate (from the red solid) shaken with 76 g. KI in H2O, decolorized with 0.345 equivalent Na2S2O3, and distilled gave 8.8 g. VII. I (10.6 g.) in 40 cc. CCl4 added during 1 h. at 0° to 12.5 g. Br in 60 cc. CCl4 gave 2.1 g. orange solid which contained 58.3% Br (dried at 0.1 mm. and 0°). I (2.6 g.) added to 6.4 g. Br in 8 cc. CCl4 at -25 to -30° gave 4.1 g. red solid containing 69.5% Br. I (30.1 g.) added at 0° during 40 min. to 20.2 g. ICl in 100 cc. CCl4 and the mixture distilled twice gave 5.4 g. MeCHClCO2Et, 9.1 g. IV, 7.9 g. V, and 5.7 g. VI. (CN)2 bubbled through 18.3 g. I at 100° with stirring during 3 h. and distilled gave only 16.0 g. unchanged I. I (51.1 g.) added slowly with stirring during 25 min. to 47.1 g. BrCN in 70 cc. Et2O and distilled gave 90.4 g. MeCHBrC(OEt)2CN (VIII), b16 108°, nD25 1.4463, d25 1.2611. I (19.6 g.) in 150 cc. Et2O treated with stirring with 18.0 g. BrCN in 50 cc. Et2O an distilled gave 28.9 g. VIII. VIII (6.00 g.) shaken 8 h. with 4.32 g. AgNO3 in 150 cc. Et2O, and the precipitate filtered, washed with Et2O, and dried gave 3.5 g. AgCN; the aqueous layer contained 0.181 mol acid; the Et2O washings distilled gave 3.5 g. VII, b14 54°, nD25 1.4427. VIII (10 g.) refluxed (210°) 5.5 h., and the HCN evolved passed into aqueous AgNO3 gave 1.2 g. AgCN; the residue distilled gave 23% impure VII, nD25 1.4414-1.4433. I (9.7 g.) added dropwise to 11.4 g. ICN in 50 cc. Et2O and distilled gave 18.5 g. MeCHIC(OEt)2CN, b0.15 84-9°, nD25 1.4798. I (11.8 g.) added with stirring to 2.45 g. HCN at -10° and distilled gave 12.2 g. II, b10 62-3°, nD25 1.4040, d25 0.9113, MRD 42.19; and 0.5 g. III, b0.25 70°, nD25 1.4330, 0.9641, MRD 77.53. I (17.1 g.) treated with cooling with 3.9 g. liquid HCN during 20 min. and the mixture kept 1.5 days at 25° and distilled gave 14.6 g. II and 4.7 g. XIII.

Compound(3400-55-3)Synthetic Route of C7H15BrO2 received a lot of attention, and I have introduced some compounds in other articles, similar to this compound(2-Bromopriopionaldehydediethylacetal), if you are interested, you can check out my other related articles.

Reference:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Ketene acetals. XXXIII. The addition of halogens and cyanogen compounds to methylketene diethyl acetal》. Authors are McElvain, S. M.; McLeish, Wm. L..The article about the compound:2-Bromopriopionaldehydediethylacetalcas:3400-55-3,SMILESS:CC(Br)C(OCC)OCC).Synthetic Route of C7H15BrO2. Through the article, more information about this compound (cas:3400-55-3) is conveyed.

cf. C.A. 49, 14687i. Salts of the type [MeCHXC(OEt)2]Xn-1 (n = 4 when X = iodine; n = 0 and 2 when X = Br) have been isolated and shown to be the intermediates through which certain dimeric products are formed when these halogens react with MeCH:C(OEt)2 (I). (CN)2 did not react with I, but both BrCN and ICN add readily to give only MeCHXC(OEt)2CN in high yields. HCN reacted exothermically with I to yield the monomeric and dimeric addition products, EtC(OEt)2CN (II) and EtC(OEt)2CHMeC(OEt)2CN (III). I (16.0 g. ) in 300 cc. Et2O at 25 ° treated with stirring with 14.4 g. iodine during 1.75 h., the solvent and EtI distilled off at 9 mm., and the residue distilled gave 3.5 g. MeCHICO2Et (IV); 2.4 g. EtC(OEt)2CMe:C(OEt)2 (V), b0.25 47°, nD25 1.4305 (V first added and then substituted Br and slowly gave a green color with FeCl3); and 14.5 g. MeCHIC(OEt)2CHMeCO2Et (VI), b0.25 92°, nD25 1.4782 (VI when treated with Br or on standing liberated iodine). VI ( 13.2 g.) heated 15 min. at 210° gave 6.86 g. EtI-EtOH azeotrope; the dark brown residue yielded 0.95 g. Et α,γ-dimethyltetronate, b. 153-68°, nD25 1.4731, which hydrolyzed gave the free acid, m. 121.5-2.5°. V (6.85 g.) and 1.52 g. H2O heated 0.5 h. with stirring at 85-95°, and the solution dried and distilled gave 2.65 g. EtCOCHMeCO2Et, which yielded a pyrazolone, m. 108-10°. I (16.5 g.) added dropwise during 1 h. to 25.2 g. iodine in 500 cc. Et2O at 25° and the solution distilled gave 18.5 g. IV and 5.3 g. VI. Iodine (2.17 g.) in 28 cc. Et2O added during 1 h. to 11.1 g. I in 117 cc. Et2O at 0° and the mixture distilled gave 8.0 g. unchanged I, 1.75 g. V, and 1.05 g. VI. Iodine (61.0 g.) in 450 cc. Et2O treated with stirring at 0-5° with 31.2 g. I during 40 min., the light yellow, supernatant liquid forced through a filter stick, the remaining solid treated with 200 cc. cold Et2O and 25 cc. cold H2O, the mixture titrated with aqueous Na2S2O3 until colorless (0.118 mol iodine was present), the aqueous layer titrated with base (0.058 mol acid present), and the Et2O layer distilled gave 11.8 g. IV; these titrations showed the salt to be [MeCHIC(OEt)2]I5. Iodine (119.8 g.) in 800 cc. Et2O treated at about -3° with 20.4 g. I during 15 min., and the heavy brown precipitate worked up and titrated in the usual manner, and finally treated with H2O gave 22.5 g. IV. Iodine (49.6 g.) and 25.4 g. mixed with 100 cc. cold Et2O, the Et2O suspension treated with 27.7 g. I, and the mixture worked up gave 6.6 g. IV, 7.0 g. V, 20.4 g. VI, and 3.5 g. unchanged I. I (10.2 g.) in 100 cc. Et2O treated with 21.3 g. iodine in 200 cc. Et2O at 0° during 3 h., and the orange solution distilled gave 18.1 g. Me2CHICO2Et, b12 64°, nD25 1.5010. I (21.0 g.) in 100 cc. CCl4 added during 35 min. with stirring at -5° to 98.5 g. Br in 200 cc. CCl4, the solvent removed through a filter stick, the residual heavy, granular, red solid shaken with 20 cc. cold H2O, the mixture treated with 100 g. KI in H2O and titrated with Na2S2O3 (0.303 mol Br present), and the organic layer extracted and distilled gave 12.2 g. MeCHBrCO2Et (VII); the CCl4 filtrate (from the red solid) shaken with 76 g. KI in H2O, decolorized with 0.345 equivalent Na2S2O3, and distilled gave 8.8 g. VII. I (10.6 g.) in 40 cc. CCl4 added during 1 h. at 0° to 12.5 g. Br in 60 cc. CCl4 gave 2.1 g. orange solid which contained 58.3% Br (dried at 0.1 mm. and 0°). I (2.6 g.) added to 6.4 g. Br in 8 cc. CCl4 at -25 to -30° gave 4.1 g. red solid containing 69.5% Br. I (30.1 g.) added at 0° during 40 min. to 20.2 g. ICl in 100 cc. CCl4 and the mixture distilled twice gave 5.4 g. MeCHClCO2Et, 9.1 g. IV, 7.9 g. V, and 5.7 g. VI. (CN)2 bubbled through 18.3 g. I at 100° with stirring during 3 h. and distilled gave only 16.0 g. unchanged I. I (51.1 g.) added slowly with stirring during 25 min. to 47.1 g. BrCN in 70 cc. Et2O and distilled gave 90.4 g. MeCHBrC(OEt)2CN (VIII), b16 108°, nD25 1.4463, d25 1.2611. I (19.6 g.) in 150 cc. Et2O treated with stirring with 18.0 g. BrCN in 50 cc. Et2O an distilled gave 28.9 g. VIII. VIII (6.00 g.) shaken 8 h. with 4.32 g. AgNO3 in 150 cc. Et2O, and the precipitate filtered, washed with Et2O, and dried gave 3.5 g. AgCN; the aqueous layer contained 0.181 mol acid; the Et2O washings distilled gave 3.5 g. VII, b14 54°, nD25 1.4427. VIII (10 g.) refluxed (210°) 5.5 h., and the HCN evolved passed into aqueous AgNO3 gave 1.2 g. AgCN; the residue distilled gave 23% impure VII, nD25 1.4414-1.4433. I (9.7 g.) added dropwise to 11.4 g. ICN in 50 cc. Et2O and distilled gave 18.5 g. MeCHIC(OEt)2CN, b0.15 84-9°, nD25 1.4798. I (11.8 g.) added with stirring to 2.45 g. HCN at -10° and distilled gave 12.2 g. II, b10 62-3°, nD25 1.4040, d25 0.9113, MRD 42.19; and 0.5 g. III, b0.25 70°, nD25 1.4330, 0.9641, MRD 77.53. I (17.1 g.) treated with cooling with 3.9 g. liquid HCN during 20 min. and the mixture kept 1.5 days at 25° and distilled gave 14.6 g. II and 4.7 g. XIII.

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Reference:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics