Selective and Efficient Generation of ortho-Brominated para-Substituted Phenols in ACS-Grade Methanol

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

Research output: Contribution to journalArticlepeer-review

Abstract / Description of output

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
Number of pages8
JournalMolecules
Volume21
Issue number1
DOIs
Publication statusPublished - 13 Jan 2016

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