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Synthesis 1986; 1986(10): 868-870
DOI: 10.1055/s-1986-31813
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Synthetic Methods and Reactions; 1271. Regioselective para Halogenation of Phenols, Phenol Ethers and Anilines with Halodimethylsulfonium Halides

George A. Olah* , Lena Ohannesian, Massoud Arvanaghi
  • *Donald P. and Katherine B. Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, Los Angeles, CA 90089-1661, U. S. A.
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Publication Date:
20 August 2002 (online)

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Halodimethylsulfonium halides [bromodimethylsulfonium bromide and chlorodimethylsulfonium chloride] are efficient regioselective para halogenating agent for activated aromatics, such as phenol, anisole, diphenyl ether and N-alkylanilines. Dihalo and monohalo derivatives of diphenyl ethers were obtained depending upon the reaction conditions. Aniline itself is not suitable in the reaction due to the strong complexation of the lone electron pair of nitrogen with the sulfonium reagent.