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Oxidative Monofluorination of 1,4-Diiodo(dibromo)-2,3,5,6-tetramethylbenzenes in the System PbO2–HF–Py–CH2Cl2

  • M. V. Kalyaev,
  • D. S. Ryabukhin,
  • A. V. Vasilyev

摘要

Abstract

The oxidation of 1,4-diiodo-2,3,5,6-tetramethylbenzene (diiododurene) and 1,4-dibromo-2,3,5,6-tetramethylbenzene (dibromodurene) with lead dioxide (PbO2) in a mixture of hydrogen fluoride and pyridine (Olahʼs reagent) and methylene chloride as co-solvent at room temperature for 96 h afforded the corresponding monofluorination products of one methyl group. This reaction is the first example of using the oxidative system PbO2–HF–Py–CH2Cl2 for the side-chain monofluorination of methylbenzenes.