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

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

Publisher： MDPI

E-ISSN： 1420-3049|21|1|88-88

ISSN： 1420-3049

Source： Molecules, Vol.21, Iss.1, 2016-01, pp. : 88-88

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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.

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