A facile, metal-free synthesis of aryl bromides using molecular bromine-an alternative to the Sandmeyer reaction

Abstract

An efficient metal-free synthesis of aryl bromides from aniline derivatives using molecular bromine is described. This one-pot reaction affords aryl bromides from corresponding electron-rich anilines in moderate to excellent yields without isolation of diazonium salts. The transformation has short reaction times, an ambient temperature, a simple workup, and insensitivity to moisture and air. This synthetic strategy represents an alternative approach to the classic Sandmeyer reaction.

Graphical abstract

A Metal-free Sandmeyer reaction strategy has been used to synthesize various aryl bromides. An aryl amines have diazotized by using sodium nitrite and 48% HBr in water and subsequently reaction mass treated with liquid bromine to offord variety of aryl bromides. Around 12 different aryl amines have been studied. Excellent yield has been obtained from electron rich aryl amine.