Promotional effect of ionic liquids in the electrophilic fluorination of phenols

Gennady I. Borodkin, Innokenty R. Elanov, Vyacheslav G. Shubin

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

Abstract

The influence of a stoichiometric amount of ionic liquids (IL) on the fluorination of phenols in various solvents has been studied. The fluorination of phenol, 1-naphthol and resorcinol was carried out using 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (F-TEDA-BF4, Selectfluor™) with the formation of 2-fluoro-, 4-fluorophenol, 2-fluoro-, 4-fluoronaphthol and 4-fluoro-, 4,6-difluoro-benzene-1,3-diol as the main products. The use of a stoichiometric amount of ionic liquid as an additive results in acceleration of the reactions. The effect is most significant at low temperatures. It has been found that solvent polarity has an essential effect on the difference in yields of fluoroproducts obtained in the presence of IL and without it.

Original languageEnglish
Pages (from-to)60-71
Number of pages12
JournalArkivoc
Volume2018
Issue number2
DOIs
Publication statusPublished - 15 Oct 2017

Keywords

  • Fluorination
  • Ionic liquid
  • Phenols
  • Solvent
  • phenols
  • REAGENTS
  • MECHANISM
  • AROMATIC-COMPOUNDS
  • ionic liquid
  • F-TEDA-BF4
  • CHEMISTRY
  • solvent
  • AGENTS
  • INHIBITORS

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