ortho‐Spezifische Bromierung von Phenolen

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.