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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 CH 3 , F, and NHBoc.

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