HALOGENATION USING N-HALOGEN COMPOUNDS .1. EFFECT OF AMINES ON ORTHO-BROMINATION OF PHENOLS WITH NBS

Authors
FUJISAKI S EGUCHI H OMURA A OKAMOTO A NISHIDA A
Citation
S. Fujisaki et al., HALOGENATION USING N-HALOGEN COMPOUNDS .1. EFFECT OF AMINES ON ORTHO-BROMINATION OF PHENOLS WITH NBS, Bulletin of the Chemical Society of Japan, 66(5), 1993, pp. 1576-1579
Citations number
12
Categorie Soggetti
Chemistry
Journal title
Bulletin of the Chemical Society of Japan → ACNP
ISSN journal
00092673
Volume
66
Issue
5
Year of publication
1993
Pages
1576 - 1579
Database
ISI
SICI code
0009-2673(1993)66:5<1576:HUNC.E>2.0.ZU;2-S
Abstract
Primary and secondary amines, especially diisopropylamine and dibutyla mine, catalyzed ortho-dibromination of phenol and ortho-monobrominatio n of 2-substituted phenols with NBS in dichloromethane to give selecti vely 2,6-dibromophenol and 2-bromo-6-substituted phenols, respectively . The effective intermediates are inferred to be N-bromoamines. The sc ope and limitations of the bromination are also presented.