Nuclear Versus Side-Chain Bromination of 4-Methoxy Toluene by an Electrochemical Method

Abstract

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 CHCl₃ 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.

GRAPHICAL ABSTRACT

Keywords:

• Aromatic compound
• bromination
• 3-bromo 4-methoxy benzyl bromide
• electrochemical
• organic phase
• two-phase electrolysis