Direct electrophilic fluorination of naproxen with NF-reagents

Gennady I. Borodkin, Innokenty R. Elanov, Yury V. Gatilov, Vyacheslav G. Shubin

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

A novel effective protocol has been developed for direct fluorination of naproxen using the electrophilic fluorinating reagents 1-chloromethy1-4-fluoro-l,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor™, F-TEDA-BF4) and N-fluorobenzenesulfonimide (NFSI) in MeCN and H2O solvents with the formation of 2-(5-fluoro-6-methoxynaphthalen-2-yl)propionic and 2-(5,5-difluoro-6-oxo-5,6-dihydronaphthalen-2-yl)propionic acids. The reaction of naproxen with an excess of Selectfluor (mol. ratio NF-reagent/naproxen = 2.2) in MeOH gives methyl 2-(5,5-difluoro-6,6-dimethoxy-5,6-dihydronaphthalen-2-yl)propionate as the main product. The mechanistic aspects of the reactions and X-ray data of products are discussed.

Original languageEnglish
Article number109412
Number of pages6
JournalJournal of Fluorine Chemistry
Volume228
DOIs
Publication statusPublished - 1 Dec 2019

Keywords

  • Mechanism of fluorination
  • Naproxen
  • NF-reagent
  • X-ray analysis
  • DISCOVERY

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