| Abstract: | Ortho-Specific Bromination of Phenols Phenol as well as 3-substituted phenols are brominated exclusively in the orthopositions by N.N-dibromomethylamine, yielding 2.6-dibrominated phenols in excellent yields. Phenols bearing an ortho-substituent need N-bromomethylamine as the brominating agent to take up one bromine atom into the free ortho-position. para-Bromination is not observed in either case. 1-Naphthol gives 2-bromo-1-naphthol, 8-hydroxyquinoline gives 7-bromo-8-hydroxyquinoline with 80% and 98% yield respectively. ortho-Specific chlorination of phenols was carried out in some cases using N-chloro-alkylamines. |
