SIMPLE AND QUICK METHOD FOR SYNTHESIS OF META-ACYLATED PHENOLS

被引：10

作者：

BENNETAU, B ^{[1
]}

RAJARISON, F ^{[1
]}

DUNOGUES, J ^{[1
]}

BABIN, P ^{[1
]}

机构：

[1] UNIV BORDEAUX 2,PHARM CHIM LAB,F-33000 BORDEAUX,FRANCE

来源：

TETRAHEDRON | 1994年 / 50卷 / 04期

关键词：

D O I：

10.1016/S0040-4020(01)80829-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new method for the meta acylation of anisole and its para-methyl or fluoro derivatives, is described. Addition of two trimethysilyl groups in the 2 and 5 positions (relative to the methoxy group), followed by hydrolysis affords the corresponding 5-trimethylsilyl-3-cyclohexenones. Electrophilic substitution of the silyl group using RCOCl/2AlCl(3) at low temperature provides, after final aromatisation promoted by Pd/C or CuBr2/LiBr, the expected meta acylated products. This mode of meta functionalization has been successfully applied to an original synthesis of ketoprofen starting from anisole.

引用

页码：1179 / 1188

页数：10

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