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

doi:10.3390/molecules21010088

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

School of Chemistry

Research output: Contribution to journal › Article › peer-review

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 language	English
Number of pages	8
Journal	Molecules
Volume	21
Issue number	1
DOIs	https://doi.org/10.3390/molecules21010088
Publication status	Published - 13 Jan 2016

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title = "Selective and Efficient Generation of ortho-Brominated para-Substituted Phenols in ACS-Grade Methanol",

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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AU - Georgiev, David

AU - Saes, Bartholomeus W H

AU - Johnston, Heather J

AU - Boys, Sarah K

AU - Healy, Alan

AU - Hulme, Alison N

PY - 2016/1/13

Y1 - 2016/1/13

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/85000634237

U2 - 10.3390/molecules21010088

DO - 10.3390/molecules21010088

M3 - Article

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SN - 1420-3049

VL - 21

JO - Molecules

JF - Molecules

IS - 1

ER -

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

Abstract

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