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Synthesis 1993; 1993(2): 237-241
DOI: 10.1055/s-1993-25839
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Ring Halogenations of Polyalkylbenzenes with N-Halosuccinimide and Acidic Catalysts

Pakorn Bovonsombat* , Edward Mcnelis
  • *Department of Chemistry, New York University, New York, New York 10003, USA
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Publication History

Publication Date:
17 September 2002 (online)

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1-Bromo-2,5-pyrrolidinedione (NBS) and 1-chloro-2,5-pyrrolidinedione (NCS) with catalytic quantities of p-toluenesulfonic acid have been used for ring halogenations of polyalkylbenzenes. [Hydroxy(tosyloxy)iodo]benzene was effective as a catalyst with NBS but not NCS. Competition experiments with 1-iodo-2,5-pyrrolidinedione (NIS) were run to indicate selectivities in substrates, halogen sources and catalysts. With this information a mixed halogenated compound, 2-bromo-4-iodo-1,3,5-trimethylbenzene was prepared in high yield.