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Synthesis 2000; 2000(8): 1078-1080
DOI: 10.1055/s-2000-6320
short paper
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Preparation of 4-Hydroxy-2-trifluoromethylthiophene: A Novel Bioisostere of α,α,α-Trifluoro-m-cresol

Gary M. Karp* , Dilip Samant, Sudarsan Mukhopadhyay, Michael E. Condon, Axel Kleemann
  • *American Cyanamid Company, Agricultural Products Research Division, P.O. Box 400, Princeton NJ, 08543-0400, USA; Fax +1 (6 09) 2 75 35 34; E-mail: Karpg@pt.cyanamid.com
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Publication Date:
31 December 2000 (online)

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A simple and convenient four-step synthesis of 4-hydroxy-2-trifluoromethylthiophene (1) a novel bioisostere of α,α,α-trifluoro-m-cresol is reported. The key step is the condensation between ethyl 3-methoxy-4,4,4-trifluorocrotonate and methyl thioglycolate to form methyl 3-hydroxy-5-trifluoromethylthiophene-2-carboxylate (6). Hydrolysis of the ester followed by decarboxylation furnishes 1. Multi-hundred gram quantities of 1 have been obtained utilizing the present procedure.

addition-reactions - cyclizations - thiophenes - Fiesselmann reaction - bioisosteres

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