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【结 构 式】

【分子编号】55804

【品名】4-Bromobenzeneboronic acid; 4-Bromophenylboronic acid

【CA登记号】5467-74-3

【 分 子 式 】C6H6BBrO2

【 分 子 量 】200.82744

【元素组成】C 35.88% H 3.01% B 5.38% Br 39.79% O 15.93%

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:(V)

The reaction of ethyl 7-bromoheptanoate (I) with NaI, Zn, dibromoethane, LiCl and CuCN gives the organometallic derivative (II), which is condensed with 4-bromobenzoyl chloride (III) in THF to yield 8-(4-bromophenyl)-8-oxooctanoic acid ethyl ester (IV). The condensation of (IV) with 4-bromophenylboronic acid (V) by means of Pd(PPh3)4 and K2CO3 in hot toluene affords 8-(4'-bromobiphenyl-4-yl)-8-oxooctanoic acid ethyl ester (VI), which is hydrolyzed with NaOH in THF/methanol to provide the corresponding carboxylic acid (VII). Finally, this compound is treated with hydroxylamine, EDC, HOBt and TEA to obtain the target hydroxamic acid.

1 Woo, S.H.; et al.; Structurally simple trichostatin A-like straight chain hydroxamates as potent histone deacetylase inhibitors. J Med Chem 2002, 45, 13, 2877.
2 Delorme, D.; Woo, S.H.; Vaisburg, A. (MethylGene Inc.); Inhibitors of histone deacetylase. WO 0170675 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 36428 ethyl 7-bromoheptanoate 29823-18-5 C9H17BrO2 详情 详情
(II) 55802   C10H17CuINO2Zn 详情 详情
(III) 45960 4-bromobenzoyl chloride 586-75-4 C7H4BrClO 详情 详情
(IV) 55803 ethyl 8-(4-bromophenyl)-8-oxooctanoate C16H21BrO3 详情 详情
(V) 55804 4-Bromobenzeneboronic acid; 4-Bromophenylboronic acid 5467-74-3 C6H6BBrO2 详情 详情
(VI) 55805 ethyl 8-(4'-bromo[1,1'-biphenyl]-4-yl)-8-oxooctanoate C22H25BrO3 详情 详情
(VII) 55806 8-(4'-bromo[1,1'-biphenyl]-4-yl)-8-oxooctanoic acid C20H21BrO3 详情 详情
Extended Information