Selective and efficient generation of ortho-brominated para-substituted phenols in ACS-grade methanol

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

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 (US)
Article number	21010088
Journal	Molecules
Volume	21
Issue number	1
DOIs	https://doi.org/10.3390/molecules21010088
State	Published - Jan 1 2016

Keywords

Acs-grade methanol
Nbs
Ortho-bromination

ASJC Scopus subject areas

Analytical Chemistry
Chemistry (miscellaneous)
Molecular Medicine
Pharmaceutical Science
Drug Discovery
Physical and Theoretical Chemistry
Organic Chemistry

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10.3390/molecules21010088

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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.",

keywords = "Acs-grade methanol, Nbs, Ortho-bromination",

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T1 - Selective and efficient generation of ortho-brominated para-substituted phenols in ACS-grade methanol

AU - Georgiev, David

AU - Saes, Bartholomews W.H.

AU - Johnston, Heather J.

AU - Boys, Sarah K.

AU - Healy, Alan

AU - Hulme, Alison N.

PY - 2016/1/1

Y1 - 2016/1/1

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.

KW - Acs-grade methanol

KW - Nbs

KW - Ortho-bromination

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JF - Molecules

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Selective and efficient generation of ortho-brominated para-substituted phenols in ACS-grade methanol

Abstract

Keywords

ASJC Scopus subject areas

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