Ring Halogenations of Polyalkylbenzenes withN-Halosuccinimide and Acidic Catalysts

Authors:
  • PBPakorn Bovonsombat
    Pakorn Bovonsombat
  • EMEdward Mcnelis
    Edward Mcnelis
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Abstract
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.