Facile Incorporation of Bromine into Aromatic Systems under Conditions of Water Chlorination

The reaction of aqueous solutions of biphenyl and naphthalene with chlorine in the presence of potassium bromide resulted in the loss of organic substrate and the formation of a series of chlorinated and brominated products. The extent of the reaction in the presence of bromide was typically greater than with chlorine alone. Chloramine (pH >6.0) and chlorine dioxide (pH 4.5-7.5) in the presence or in the absence of bromide resulted in no substantial loss of biphenyl or naphthalene.