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Molecules 2016, 21(1), 88; doi:10.3390/molecules21010088

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

EaStCHEM School of Chemistry, The University of Edinburgh, David Brewster Road, Edinburgh EH9 3FJ, UK
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Academic Editor: Kerry Gilmore
Received: 28 September 2015 / Revised: 23 December 2015 / Accepted: 7 January 2016 / Published: 13 January 2016
(This article belongs to the Section Organic Synthesis)
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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. View Full-Text
Keywords: ortho-bromination; ACS-grade methanol; NBS ortho-bromination; ACS-grade methanol; NBS
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MDPI and ACS Style

Georgiev, D.; Saes, B.W.H.; Johnston, H.J.; Boys, S.K.; Healy, A.; Hulme, A.N. Selective and Efficient Generation of ortho-Brominated para-Substituted Phenols in ACS-Grade Methanol. Molecules 2016, 21, 88.

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