Silica gel catalyzed conversion of dimethyl 2-(5-bromo-2-hydroxyphenyl)-3-(triphenylphosphoranylidene)butanedioate to methyl 6-bromo-2-oxo-2H-chromene-4-carboxylate in solvent-free conditions

被引：46

作者：

Ramazani, A ^{[1
]}

Souldozi, A ^{[1
]}

机构：

[1] Zanjan Univ, Dept Chem, Zanjan, Iran

来源：

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS | 2003年 / 178卷 / 12期

关键词：

4-bromophenol; chromene; dimethyl acetylenedicarboxylate; silica gel; vinyltriphenylphosphonium salt;

D O I：

10.1080/714040980

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Protonation of the highly reactive 1:1 intermediates, produced in the reaction between triphenylphosphine and dimethyl acetylenedicarboxylate, by 4-bromophenol leads to vinyltriphenylphosphonium salt, which undergoes aromatic electrophilic substitution reaction with conjugate base to produce dimethyl 2-(5-bromo-2-hydroxyphenyl)3-(triphenylphosphoranylidene)butanedioate. Silica gel was found to catalyze conversion of dimethyl 2-(5-bromo-2-hydroxyphenyl)-3-(triphenylphosphoranylidene)butanedioate to methyl 6-bromo-2-oxo-2H-chromene-4-carboxylate in solvent-free conditions at 80degreesC in fairly high yield.

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收藏

页码：2663 / 2666

页数：4

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