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Paper | Regular issue | Vol 34, No. 1, 1992, pp.149-156
Published online, 1st January, 1970
DOI: 10.3987/COM-91-5907
A Convenient Synthesis of 3(2)-Trifluoroacetylaminobenzo[b]thiophenes and Thiophenes and Some of Their Iodo Derivatives

Montserrat Prats* and Carmen Gálvez

*Departament de Química Orgánica, Facultat de Química, Universitat de Barcelona, Martí i Franquès 1-11, 08028 Barcelona, Spain


Trifluoroacetylamino derivatives of benzo[b]thiophene (3a-d) have been obtained by Curtius rearrangement of the corresponding acyl azides (1a-d) with trifluoroacetic acid. The iodination of these amide derivatives with iodine under mild conditions leads to iodinated products in excellent yield, except in the case of the 3-trifluoroacetylaminobenzo[b]thiophene (3a), which only gives a polymeric residue.