The electrochemical bromination of 4-methoxy toluene by two-phase electrolysis yields 3-bromo 4-methoxy toluene at first, which subsequently undergoes side-chain bromination to give 3-bromo 4-methoxy benzyl bromide as a final product in 86% yield. The two-phase electrolysis consists of 25-50% NaBr as aqueous electrolyte and CHCl 3 containing aromatic compound as organic phase. The reaction temperature is maintained at 10-25 C. The probable orientation of bromine atom in an alkyl aromatic compound (nuclear versus side chain) is explained from the experimental result.

No abstract

Nuclear versus Side-Chain Bromination of 4-Methoxy Toluene by an Electrochemical Method. -The electrochemical bromination of substituted toluenes is described. The results can be explained by known mesomeric and inductive effects. -(KULANGIAPPAR, K.; ANBUKULANDAINATHAN, M.; RAJU*, T.; Synth. Commun. 44 (2014) 17, 2494-2502, http://dx.