An alternative synthesis of chlorinated biphenyl methylsulfonyl metabolites

Article abstract of DOI:10.1016/0045-6535(95)00331-2

Published methods of synthesizing chlorinated biphenyl methylsulfones require the separation of a complex mixture of impurities and isomers using both normal and reverse phase HPLC. Even with semi-preparative scale equipment, the process is tedious and time-consuming. In this report, the palladium-catalyzed addition of an aryl iodide to an aryl trimethylstannane has been exploited to produce these compounds in high purity (≥ 99%) using conventional techniques of purification. The reaction has been demonstrated for a group of methylsulfonyl CBs representing 0 to 3 ortho-chlorine interactions between the biphenyl rings and with the methylsulfonyl group at either the 3- or 4- position.