Journal of Heterocyclic Chemistry p. 1247 - 1251 (1999)
Update date:2022-08-03
Topics:
Kobarfard, Farzad
Kauffman, Joel M.
Boyko, Walter J.
It appeared that a key intermediate for 2-amino-3-fluorothiophene (1), methyl 3-fluorothiophene-2-carboxylate (5), had been prepared by a Schiemann reaction of the 3-diazonium salt (6) in xylenes. This report was not correct. Gomberg coupling products 7 with o-xylene are actually formed. We were able to prepare 5 by using special conditions for the Schiemann reaction. The hydrazide derivative of 5 failed to give 1 under Curtius reaction conditions. Two new acetamidofluorothiophene compounds were prepared using Selectfluor(TM) as the fluorinating agent, but no aminofluorothiophenes 1-3 or salts could be obtained by acidic hydrolysis of either amide.
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