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【结 构 式】

【分子编号】54804

【品名】4,7-dichloro-1-benzothiophene

【CA登记号】

【 分 子 式 】C8H4Cl2S

【 分 子 量 】203.09116

【元素组成】C 47.31% H 1.99% Cl 34.91% S 15.79%

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:(IV)

Alkylation of 2,5-dichlorothiophenol (I) with bromoacetaldehyde diethyl acetal (II) produced thioether (III). Benzothiophene (IV) was then obtained by cyclization of (III) under Friedel-Crafts conditions in the presence of polyphosphoric acid. Metalation of benzothiophene (IV) with BuLi at -78 C, followed by addition of sulfur dioxide gave rise to the sulfinic acid (V). This was converted to the sulfonyl chloride (VI) by chlorination with N-chlorosuccinimide, and further treatment of (VI) with ammonium hydroxide provided the sulfonamide (VII). Addition of formaldehyde to the benzothiophene-2-sulfonamide (VII), followed by condensation with trimethyl phosphite, furnished the dimethyl (sulfonamidomethyl)phosphonate (VIII). The phosphonate ester function of (VIII) was then hydrolyzed by means of bromotrimethylsilane, producing phosphonic acid (IX). This was finally coupled to 4-nitrophenol (X) using trichloroacetonitrile in hot pyridine to afford the title mono-phosphonate ester.

1 Delorme, D.; Besterman, J.M.; Rahil, J. (MethylGene Inc.); Sulfonamidomethyl phosphonate inhibitors of beta-lactamase. EP 1194436; WO 0102411 .
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) 54802 2,5-Dichlorobenzenethiol; 2,5-Dichlorophenylmercaptan; 2,5-Dichlorothiophenol 5858-18-4 C6H4Cl2S 详情 详情
(II) 12113 2-Bromo-1-ethoxyethyl ethyl ether; 2-Bromo-1,1-diethoxyethane; Bromoacetaldehyde diethylacetal 2032-35-1 C6H13BrO2 详情 详情
(III) 54803 2-[(2,5-dichlorophenyl)sulfanyl]-1-ethoxyethyl ethyl ether; 1,4-dichloro-2-[(2,2-diethoxyethyl)sulfanyl]benzene C12H16Cl2O2S 详情 详情
(IV) 54804 4,7-dichloro-1-benzothiophene C8H4Cl2S 详情 详情
(V) 54805 4,7-dichloro-1-benzothiophene-2-sulfinic acid C8H4Cl2O2S2 详情 详情
(VI) 54806 4,7-dichloro-1-benzothiophene-2-sulfonyl chloride C8H3Cl3O2S2 详情 详情
(VII) 54807 4,7-dichloro-1-benzothiophene-2-sulfonamide C8H5Cl2NO2S2 详情 详情
(VIII) 54808 dimethyl {[(4,7-dichloro-1-benzothiophen-2-yl)sulfonyl]amino}methylphosphonate C11H12Cl2NO5PS2 详情 详情
(IX) 54809 {[(4,7-dichloro-1-benzothiophen-2-yl)sulfonyl]amino}methylphosphonic acid C9H8Cl2NO5PS2 详情 详情
(X) 11236 4-Nitrophenol; p-Nitrophenol 100-02-7 C6H5NO3 详情 详情
Extended Information