Selective and efficient generation of ortho-brominated para-substituted phenols in ACS-grade methanol

David Georgiev, Bartholomews W.H. Saes, Heather J. Johnston, Sarah K. Boys, Alan Healy, Alison N. Hulme

Research output: Contribution to journalArticle

Abstract

The mono ortho-bromination of phenolic building blocks by NBS has been achieved in short reaction times (15-20 min) using ACS-grade methanol as a solvent. The reactions can be conducted on phenol, naphthol and biphenol substrates, giving yields of >86% on gram scale. Excellent selectivity for the desired mono ortho-brominated products is achieved in the presence of 10 mol % para-TsOH, and the reaction is shown to be tolerant of a range of substituents, including CH3/ F,and NHBoc.

Original languageEnglish (US)
Article number21010088
JournalMolecules
Volume21
Issue number1
DOIs
StatePublished - Jan 1 2016

Keywords

  • Acs-grade methanol
  • Nbs
  • Ortho-bromination

ASJC Scopus subject areas

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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