The effect of substituents separated from an aromatic ring by an intervening amide functionality on the rate of electrophilic aromatic bromination of anilides and related compounds was investigated. The anilides with activating and deactivating substituents were synthesized, and each compound was subsequently brominated with Br2 in glacial acetic acid. Bromination rates were determined by spectrophotometrically monitoring the rate of disappearance of bromine. Hammett plots and reaction constants were analyzed to assess the effect of each substituent on the rate of bromination. The results demonstrate significant substituent effects in electrophilic aromatic bromination by groups that are not directly attached to the aromatic ring. These results are of interest due to the importance of brominated aromatic compounds in the synthesis of various chemical products.

Substituent effects in electrophilic aromatic bromination of anilides

245th National Meeting (2013)

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