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【结 构 式】

【分子编号】68419

【品名】1-(3-bromo-5-(tert-butyl)-4-hydroxyphenyl)ethanone

【CA登记号】 

【 分 子 式 】C12H15BrO2

【 分 子 量 】271.1539

【元素组成】C 53.16% H 5.58% Br 29.47% O 11.8%

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:(XXV)

Bromination of 1-(3-tert-butyl-4-hydroxyphenyl)ethanone (III) with NBS in acetonitrile yields 1-(3-bromo-5-tert-butyl-4-hydroxyphenyl)ethanone (XXV), which by protection with trimethyl orthoformate (XXVI) in the presence of (±)-CSA in MeOH affords the dimethyl acetal (XXVII). O-Methylation of phenol (XXVII) with MeI by means of K2CO3 in DMF provides 1-bromo-3-tert-butyl-5-(1,1-dimethoxyethyl)-2-methoxybenzene (XXVIII), which by Buchwald–Hartwig condensation with morpholine (XXIX) in the presence of Pd(OAc)2, BINAP and t-BuONa in DME leads to the Narylmorpholine (XXX). Bromination of compound (XXX) with PhNMe3Br3 in THF/MeOH generates the α-bromoacetal (XXXI), which, without isolation, is finally hydrolyzed by quenching in aqueous Na2S2O3 to give bromo ketone (IX) .

1 Shimomura, N., Sasho, M., Kayano, A., Yoshizawa, K., Tsujii, M., Kuroda,H., Furukawa, K. (Eisai R&D Management Co., Ltd.). Processes for producing cyclic benzamidine derivative. CA 2515715, EP 1602646, US 2006058370, US 7375236, WO 2004078721.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XXX) 68422 4-(3-(tert-butyl)-5-(1,1-dimethoxyethyl)-2-methoxyphenyl)morpholine   C19H31NO4 详情 详情
(III) 68400 1-(3-tert-butyl-4-hydroxyphenyl)ethanone   C12H16O2 详情 详情
(IX) 68405 2-bromo-1-(3-(tert-butyl)-4-methoxy-5-morpholinophenyl)ethanone   C17H24BrNO3 详情 详情
(XXV) 68419 1-(3-bromo-5-(tert-butyl)-4-hydroxyphenyl)ethanone   C12H15BrO2 详情 详情
(XXVI) 27311 trimethoxymethane;Trimethyl orthoformate;Methyl orthoformate 149-73-5 C4H10O3 详情 详情
(XXVII) 68420 2-bromo-6-(tert-butyl)-4-(1,1-dimethoxyethyl)phenol   C14H21BrO3 详情 详情
(XXVIII) 68421 1-bromo-3-(tert-butyl)-5-(1,1-dimethoxyethyl)-2-methoxybenzene;1-bromo-3-tert-butyl-5-(1,1-dimethoxyethyl)-2-methoxybenzene   C15H23BrO3 详情 详情
(XXIX) 10388 Morpholine 110-91-8 C4H9NO 详情 详情
(XXXI) 68423 4-(5-(2-bromo-1,1-dimethoxyethyl)-3-(tert-butyl)-2-methoxyphenyl)morpholine   C19H30BrNO4 详情 详情
Extended Information