A new strategy for the synthesis of polychlorinated biphenyl metabolites

A general and high-yielding synthetic route is presented by which a variety of chlorinated dihydroxybiphenyl metabolites may be synthesized. These synthetic standards will permit the investigation of novel pathways of polychlorinated biphenyl activation. The biphenyldiols were synthesized via palladium-catalyzed cross-coupling of dimethoxyphenylboronic acids with aryl bromides in the presence of a base. The formed dimethoxybiphenyls were demethylated using boron tribromide to yield the chlorinated dihydroxybiphenyls. These compounds were characterized by IR, NMR, and GC/MS.