100477-84-7Relevant academic research and scientific papers
Ortho-Specific Bromination of Phenols
Schmitz, Ernst,Pagenkopf, Ingeborg
, p. 998 - 1006 (2007/10/02)
Phenol as well as 3-substituted phenols are brominated exclusively in the ortho positions 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 80percent and 98percent yield respectively. ortho-Specific chlorination of phenols was carried out in some cases using N-chloro-alkylamines.
