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Synthesis 2008(15): 2333-2336
DOI: 10.1055/s-2008-1067170
DOI: 10.1055/s-2008-1067170
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
A Facile and Improved Synthesis of 3-Fluorothiophene
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