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【结 构 式】

【分子编号】34130

【品名】2-bromo-4-(trifluoromethyl)benzoic acid

【CA登记号】

【 分 子 式 】C8H4BrF3O2

【 分 子 量 】269.0177696

【元素组成】C 35.72% H 1.5% Br 29.7% F 21.19% O 11.89%

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:(II)

The Sandmeyer reaction of 4-trifluoromethylanthranilic acid (I) with NaNO2, HBr and Cu2Br2 gives 2-bromo-4-trifluoromethylbenzoic acid (II), which by reaction with SOCl2 is converted into 2-bromo-4-trifluoromethylbenzoyl chloride (III). The Rosemind reduction of (III) with H2 over Pd/BaSO4/S yields 2-bromo-4-trifluoromethylbenzaldehyde (IV), which is condensed with ethyl cyanacetate (V) in refluxing toluene affording ethyl 2-cyano-3-[2-bromo-4-(trifluoromethyl)phenyl]propenoate (VI). The addition of 4-fluorophenylmagnesium bromide (VII) to (VI) in toluene ether gives ethyl 2-cyano-3-[2-bromo-4-(trifluoromethyl)phenyl]-3-(4-fluorophenyl)propanoate (VIII), which is hydrolyzed and decarboxylated partially with H2SO4 in refluxing acetic acid water to yield 3-[2-bromo-4-(trifluoromethyl)phenyl]-3-(4-fluorophenyl)propanoic acid (IX). Cyclization of (IX) with butyllithium in ether affords 3-(4-fluorophenyl)-6-(trifluoromethyl)indan-1-one (X), which is reducted with NaBH4 in methanol giving 3-(4-fluorophenyl)-6-(trifluoromethyl)indan-1-ol (XI). The reaction of (XI) with SOCl2 in hot toluene yields 1-chloro-3-(4-fluorophenyl)-6-(trifluoromethyl)indan (XII).

1 Castaner, J.; Serradell, M.N.; Tefludazine. Drugs Fut 1984, 9, 5, 346.
2 Bogeso, K.P.; Neuroleptic activity and dopamine-uptake inhibition in 1-piperazino-3-phenylindans. J Med Chem 1983, 26, 7, 935-947.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XIa) 34137 (1S,3R)-3-(4-fluorophenyl)-6-(trifluoromethyl)-2,3-dihydro-1H-inden-1-ol C16H12F4O 详情 详情
(XIb) 34138 (1S,3S)-3-(4-fluorophenyl)-6-(trifluoromethyl)-2,3-dihydro-1H-inden-1-ol C16H12F4O 详情 详情
(XIIa) 34139 (1R,3S)-3-chloro-1-(4-fluorophenyl)-5-(trifluoromethyl)-2,3-dihydro-1H-indene C16H11ClF4 详情 详情
(XIIb) 34140 (1S,3S)-3-chloro-1-(4-fluorophenyl)-5-(trifluoromethyl)-2,3-dihydro-1H-indene C16H11ClF4 详情 详情
(I) 34129 2-amino-4-(trifluoromethyl)benzoic acid C8H6F3NO2 详情 详情
(II) 34130 2-bromo-4-(trifluoromethyl)benzoic acid C8H4BrF3O2 详情 详情
(III) 34131 2-bromo-4-(trifluoromethyl)benzoyl chloride C8H3BrClF3O 详情 详情
(IV) 34132 2-bromo-4-(trifluoromethyl)benzaldehyde C8H4BrF3O 详情 详情
(V) 11877 Cyanoacetic acid ethyl ester; Ethyl 2-cyanoacetate; Ethyl cyanoacetate; Ethyl isocyanacetate 105-56-6 C5H7NO2 详情 详情
(VI) 34133 ethyl (Z)-3-[2-bromo-4-(trifluoromethyl)phenyl]-2-cyano-2-propenoate C13H9BrF3NO2 详情 详情
(VII) 13643 4-fluorophenyl magnesium bromide;Bromo(4-fluorophenyl)magnesium;bromo(p-fluorophenyl)Magnesium;p-Fluorophenylmagnesium bromide 352-13-6 C6H4BrFMg 详情 详情
(VIII) 34134 ethyl 3-[2-bromo-4-(trifluoromethyl)phenyl]-2-cyano-3-(4-fluorophenyl)propanoate C19H14BrF4NO2 详情 详情
(IX) 34135 3-[2-bromo-4-(trifluoromethyl)phenyl]-3-(4-fluorophenyl)propionic acid C16H11BrF4O2 详情 详情
(X) 34136 3-(4-fluorophenyl)-6-(trifluoromethyl)-1-indanone C16H10F4O 详情 详情
Extended Information