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Updated: Jul 19, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Exceptionally mild, high-yield synthesis of alpha-fluoro acrylates
1Department of Chemistry, The City College and The City University of New York, 138th Street at Convent Avenue, New York, New York 10031, USA. barbaraz@sci.ccny.cuny.edu
Abstract:
Novel achiral and chiral alkyl alpha-(1,3-benzothiazol-2-ylsulfonyl)-alpha-fluoroacetates can be readily synthesized by metalation-fluorination of (1,3-benzothiazol-2-ylsulfonyl)acetates. DBU-mediated condensations of these fluorinated synthons with aldehydes proceed in a facile manner at 0 degrees C or at room temperature giving high yields of alpha-fluoro acrylates. Ketones are unreactive under these conditions. The presence of fluorine renders the synthon substantially more reactive compared to the unfluorinated analogue. Reactivity of alpha-(1,3-benzothiazol-2-ylsulfonyl)-alpha-fluoroacetate and the Horner-Wadsworth-Emmons reagent (EtO)2P(O)CHFCOOEt has also been compared.
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