2-bromo-1-(3-chlorophenyl)-1-ethanone -Drug Synthesis Database

【结构式】

【分子编号】32824

【品名】2-bromo-1-(3-chlorophenyl)-1-ethanone

【CA登记号】

【分子式】C₈H₆BrClO

【分子量】233.49174

【元素组成】C 41.15% H 2.59% Br 34.22% Cl 15.18% O 6.85%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(XII)

The chiral intermediate 2(R)-(3-chlorophenyl)oxirane (X) has been obtained as follows: The bromination of 3'-chloroacetophenone (XI) with Br2 in acetic acid gives the 3'-chlorophenacyl bromide (XII), which is treated with dimethylamine in toluene yielding 3'-chloro-2-(dimethylamino)acetophenone (XIII). The hydrogenation of (XIII) with H2 over a chiral Rh catalyst affords the (R)-alcohol (XIV), which is finally treated with NaOH in chloroform to provide the intermediate oxirane (X).

参考文献中间体

合成目标

【1】 Devocelle, M.; et al.; Alternative synthesis of the chiral atypical beta-adrenergic phenylethanolaminotetraline agonist SR58611A using enantioselective hydrogenation. Tetrahedron Lett 1999, 40, 24, 4551.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(X)	15271	(R)-(+)-3-Chlorostyrene oxide; (2R)-2-(3-Chlorophenyl)oxirane	62600-71-9	C₈H₇ClO	详情	详情
(XI)	15268	m-chloroacetophenone; 1-(3-chlorophenyl)-1-ethanone	99-02-5	C₈H₇ClO	详情	详情
(XII)	32824	2-bromo-1-(3-chlorophenyl)-1-ethanone		C₈H₆BrClO	详情	详情
(XIII)	32825	1-(3-chlorophenyl)-2-(dimethylamino)-1-ethanone		C₁₀H₁₂ClNO	详情	详情
(XIV)	32826	(1R)-1-(3-chlorophenyl)-2-(dimethylamino)-1-ethanol		C₁₀H₁₄ClNO	详情	详情

Extended Information