Halogenation Using N-Halogenocompounds. I. Effect of Amines on ortho-Bromination of Phenols with NBS

Article abstract of DOI:10.1246/bcsj.66.1576

Primary and secondary amines, especially diisopropylamine and dibutylamine, catalyzed ortho-dibromination of phenol and ortho-monobromination of 2-substituted phenols with NBS in dichloromethane to give selectively 2,6-dibromophenol and 2-bromo-6-sybstituted phenols, respectively.The effective intermediates are inferred to be N-bromoamines.The scope and limitations of the bromination are also presented.