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A Convenient Synthesis of 3,5-bis(Trifluoromethyl)Salicylic Acid

 

作者: Zhihua Sui,   MarkJ. Macielag,  

 

期刊: Synthetic Communications  (Taylor Available online 1997)
卷期: Volume 27, issue 20  

页码: 3581-3590

 

ISSN:0039-7911

 

年代: 1997

 

DOI:10.1080/00397919708007080

 

出版商: Taylor & Francis Group

 

数据来源: Taylor

 

摘要:

A convenient method is reported for the synthesis of the biologically important intermediate, 3,5-bis(trifluoromethyl)-salicylic acid, by a sequence involving diazotization/iodination of 2-bromo-3,5-bis(trifluoromethyl)aniline, displacement of the bromide with sodium methoxide, and carboxylation of the anion generated by lithium-iodine exchange with carbon dioxide. Alternatively, the anion could be carbonylated with dimethylformamide and the resulting aldehyde oxidized with Jones reagent. Demethylation of 3,5-bis(trifluoromethyl)anisic acid with boron tribromide gave the title compound.

 

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