A Facile and Improved Synthesis of 3-Fluorothiophene

Abstract

A new efficient and convenient route to 3-fluoro­thiophene in four steps and 49% overall yield is reported. The fluorine atom was successfully introduced into the thiophene ring in 67% yield using the Schiemann reaction on 2-methoxycarbonyl­thiophene-3-diazonium tetrafluoroborate. The product, methyl 3-fluorothiophene-2-carboxylate was saponified and the 3-fluorothiophene-2-carboxylic acid was decarboxylated to afford 3-fluorothiophene in 93% yield.

Key words

heterocycles - fluorine substitution - nucleophilic aromatic substitution - 3-fluorothiophene - Schiemann reaction

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