Synthesis of α-fluorocarboxylates from the corresponding acids using acetyl hypofluorite

S. Rozen*, A. Hagooly, R. Harduf

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

α-Fluorocarboxylic esters and acids were synthesized in good yields. The corresponding esters and acids were converted to their ketene acetals, and these enol derivatives reacted with AcOF made directly from fluorine. This route circumvents the problems associated with nucleophilic fluorinations such as various eliminations and rearrangements. α- and β-branched carboxylic acid derivatives that cannot be directly fluorinated gave by this electrophilic fluorination the corresponding α-fluoro derivatives in good yield. Both the fluorination reaction and the preparation of AcOF are fast and suitable for [18]F incorporation into acids and esters needed for working with PET. α-Fluoroibuprofen (20) and methyl 2-fluoro-3,3,3-triphenylpropionate (32) are two examples of this general reaction.

Original languageEnglish
Pages (from-to)7464-7468
Number of pages5
JournalJournal of Organic Chemistry
Volume66
Issue number22
DOIs
StatePublished - 2 Nov 2001

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