A facile and improved synthesis of 3-fluorothiophene

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-methoxycarbonyl-thiophene-3-diazonium tetrafluoroborate. The product, methyl...

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Bibliographic Details
Published inSynthesis (Stuttgart) no. 15; pp. 2333 - 2336
Main Authors Pomerantz, Martin, Turkman, Nashaat
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.08.2008
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Schiemann reaction
N-METHYLPYRROLE
3-fluorothiophene
heterocycles
fluorine substitution
nucleophilic aromatic substitution
FLUORINATION
THIOPHENE
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Summary: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-methoxycarbonyl-thiophene-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.
ISSN:0039-7881
DOI:10.1055/s-2008-1067170