The innovation of our procedure for the bromination of activated aromatic compounds is twofold in that highly regiospecific p-bromination of such aryls by treatment with NBS has been accomplished with utilization of unusual reaction mediums, such as cyclohexane, acetone, and acetonitrile. The significant yields of the p-brominated products formed along with the very short reaction times using acetone or acetonitrile make this procedure most attractive by use of these unusual and affordable reaction media. That this regiospecific p-substitution takes place under such mild conditions leads us to question whether the mechanism is EAS.<br/>Thus, the use of NBS and the novel use of these unusual media under the mild reaction conditions and simple workup affords a practical method for the synthesis of mono- and dibromo compounds of substituted aromatics without the use of acids or catalysts, thereby providing a much safer, greener, faster and more efficient approach to p-brominations.

<i>p</i>-Halogenations made easy

253rd National Meeting (2017)

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p-Halogenations made easy