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1 Polish Journal of Applied Chemistry

1 2007

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Transformations of chlorodibromomethyl-4-chlorophenyl sulfone into new compounds with potential pesticidal activity

Ochal Z., Wójcicki J.

Polish Journal of Applied Chemistry

2007

Vol. 51, nr 1-2

29-41

The synthesis of chlorodibromomethyl-4-cfilorophcnyl sulfone derivatives as new potential pesticides is reported. The title sulfonc was obtained starting from chlorobenzene, its chlorosulfonation, reduction to the sulfinyl salt, which was transformed with bromofbrm or diehloroacetic acid natrium salt to dibromo-mcthyl-4-ch!orophenylsulfonc 4, or chloromcthyl-4-clilorophcnylsulfone 5. Sulfone 4 was chlorinated by hypohalite and sulfone 5 was brominated by bromine chloride or hypobromite to a final product 6. Chlorodibromomethyl-4-chiorophenyl sulfone was nitrated and then subjected to the SNAr reaction with amines and hydrazine to give 2-nitroaniline and 2-nitrophenylhydra7ioe derivatives. The last one was rransfonncd into hydrazonc, semicarbazide and tiosemicarbazidc derivatives.