Gram-Scale Preparation of Acyl Fluorides and Their Reactions with Hindered Nucleophiles
Michał Tryniszewski, Michał Barbasiewicz*
*Faculty of Chemistry, University of Warsaw, Pasteura 1, 02-093 Warsaw, Poland, Email: barbasiewiczchem.uw.edu.pl
M. Tryniszewski, M. Barbasiewicz, Synthesis, 2022, 54, 1446-1460.
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A series of acyl fluorides was conveniently synthesized at 100 mmol scale using phase-transfer-catalyzed halogen exchange between acyl chlorides and aqueous bifluoride solution. The procedure consists of vigorous stirring at room temperature, followed by extraction and distillation. Isolated acyl fluorides display excellent purity and can be transformed into sterically hindered amides and esters.
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acyl fluorides, phase-transfer catalysis, directed ortho-metalation, amides, esters