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Keywords:

  • N-Bromosuccinimide;
  • Aromatic substitution;
  • Phenols;
  • Alkoxybenzenes;
  • Bromobenzene;
  • Regioselectivity

Abstract

A comparative study of the advantages of using THF compared with DMF in regioselective monobromination reactions of highly activated polyphenols, their ethers, and their tert-butyl carbonate derivatives under mild conditions is described. Bromination with the common reagent N-bromosuccinimide in polar solvents provided an easy and fast approach to aromatic electrophilic substitution at the most electronically favored positions with respect to O-substituents. Tight control of the reaction temperature as well as short reaction times afforded better isolated yields (from 70 % to quantitative) of bromides when THF was used as the solvent instead of the classically used DMF. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)