Synthesis, volume 2008, issue 15, pages 2333-2336

A Facile and Improved Synthesis of 3-Fluorothiophene

MARTIN POMERANTZ 1
, 
Nashaat Turkman 2
1
 
Department of Chemistry & Biochemistry
2
 
Publication type: Journal Article
Publication date: 2008-07-08
Journal: Synthesis
scimago Q2
SJR: 0.582
CiteScore: 4.5
Impact factor: 2.2
ISSN: 00397881, 1437210X
Catalysis
Organic Chemistry
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.
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