Selective and Efficient Generation of ortho-Brominated para-Substituted Phenols in ACS-Grade MethanolReport as inadecuate




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EaStCHEM School of Chemistry, The University of Edinburgh, David Brewster Road, Edinburgh EH9 3FJ, UK





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Academic Editor: Kerry Gilmore

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





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

Source: http://mdpi.com/



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