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【结 构 式】

【分子编号】32699

【品名】(4-chlorophenyl)(5-fluoro-2-hydroxyphenyl)methanone

【CA登记号】62433-26-5

【 分 子 式 】C13H8ClFO2

【 分 子 量 】250.6564232

【元素组成】C 62.29% H 3.22% Cl 14.14% F 7.58% O 12.77%

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 p-chlorobenzoic acid (I) with SOCl2 gives p-chlorobenzoyl chloride (II), which is esterified with 4-fluorophenol (III) affording 4-fluorophenyl-4-chlorobenzoate (IV). The isomerization of (IV) with AlCl3 yields 4-chloro-2'-hydroxy-5'-fluorobenzophenone (V), which is condensed with 4-aminobutyric acid (VI) by means of sodium methoxide in ethanol giving 4-[[alpha-(p-chlorophenyl)-5-fluoro-2-hydroxybenzylidene]amino]butyric acid (VII). The reaction of (VII) with SOCl2 in THF affords the corresponding acyl chloride (VIII), which is then treated with NH3. An alternative way of converting the acid (VII) into its amide is by treatment with carbonyldiimidazole (A) and liquid NH3 in THF.

1 Kaplan, J.P.; et al.; Derives alpha-phenyl-benzylideniques des acides amines. FR 2358887 .
2 Kaplan, J.P.; et al. (Sanofi-Synthelabo); Benzylidene derivatives. ES 450300; FR 2319338; GB 1506808; JP 52019644; US 4094992 .
3 Kaplan, J.P.; et al. (Sanofi-Synthelabo); Preparation of benzylidene derivatives. DE 2830034; ES 471606; FR 2397397; GB 2001066; JP 54019953 .
4 Serradell, M.N.; Owen, R.T.; Blancafort, P.; Castaner, J.; Progabide. Drugs Fut 1980, 5, 9, 445.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(A) 11353 1,1'-Carbonyldiimidazole; Di(1H-imidazol-1-yl)methanone; N,N-Carbonyldiimidazole; 1,1'-Carbonylbis(1H-imidazole) 530-62-1 C7H6N4O 详情 详情
(I) 18359 p-chlorobenzoic acid; 4-chlorobenzoic acid 74-11-3 C7H5ClO2 详情 详情
(II) 10295 p-Chlorobenzoyl chloride; 4-Chlorobenzoyl chloride 122-01-0 C7H4Cl2O 详情 详情
(III) 19639 4-fluorophenol 371-41-5 C6H5FO 详情 详情
(IV) 32698 4-Fluorophenyl 4-chlorobenzoate C13H8ClFO2 详情 详情
(V) 32699 (4-chlorophenyl)(5-fluoro-2-hydroxyphenyl)methanone 62433-26-5 C13H8ClFO2 详情 详情
(VI) 13620 4-Amino-n-butyric acid; 4-Aminobutyric acid;Piperidinic acid;Piperidic acid 56-12-2 C4H9NO2 详情 详情
(VII) 32700 4-[[(Z)-(4-chlorophenyl)(5-fluoro-2-hydroxyphenyl)methylidene]amino]butyric acid C17H15ClFNO3 详情 详情
(VIII) 32701 4-[[(Z)-(4-chlorophenyl)(5-fluoro-2-hydroxyphenyl)methylidene]amino]butanoyl chloride C17H14Cl2FNO2 详情 详情
Extended Information