An alternative synthesis of chlorinated biphenyl methylsulfonyl metabolites

Published methods of synthesizing chlorinated biphenyl methylsulfonys 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-c...

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Bibliographic Details
Published in:Chemosphere (Oxford) 1996-03, Vol.32 (5), p.935-946
Main Authors: Mortimer, Richard D., Newsome, W.Harvey
Format: Article
Language:English
Subjects:
Catalysis
Catalytic reactions
Chemistry
Exact sciences and technology
General and physical chemistry
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
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Summary:Published methods of synthesizing chlorinated biphenyl methylsulfonys 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.
ISSN:0045-6535
1879-1298
DOI:10.1016/0045-6535(95)00331-2