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Updated: Jul 9, 2025

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Deoxyfluorination of Carboxylic Acids via an In Situ Generated Trifluoromethoxide Salt
Al Vicente Riano D Lisboa1, Geraldo Duran-Camacho1, Annika K Ehrlacher1
1Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan 48109, United States.
Abstract:
An in situ generated pyridinium trifluoromethoxide salt (PyOCF3) is a highly effective deoxyfluorination reagent for the synthesis of acid fluorides. PyOCF3 is formed at room temperature from the reaction of 2,4-dinitro(trifluoromethoxy)benzene with 4-dimethylaminopyridine. PyOCF3 undergoes slow release of fluorophosgene and fluoride, which serve as the electrophile and nucleophile, respectively, for deoxyfluorination. A wide substrate scope and high functional group tolerance are demonstrated. Furthermore, the acid fluorides can be purified by filtration and telescoped to various known reactions.
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