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Synthesis 2008(15): 2333-2336  
DOI: 10.1055/s-2008-1067170
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Facile and Improved Synthesis of 3-Fluorothiophene

Martin Pomerantz*, Nashaat Turkman
Department of Chemistry and Biochemistry, Box 19065, The University of Texas at Arlington, Arlington, TX 76019-0065, USA
Fax: +1(817)2723808; e-Mail: pomerantz@uta.edu;
Further Information

Publication History

Received 29 January 2008
Publication Date:
08 July 2008 (online)

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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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