THE NITRATION AND BROMINATION OF 2-(PENTAFLUOROSULFANYL)-1,3-BENZOTHIAZOLE AND 2-(TRIFLUOROMETHYL)-1,3-BENZOTHIAZOLE

Abstract

The nitration and halogenation reactions of 2-(pentafluorosulfanyl)- and 2-(trifluoromethyl)-1,3-benzothiazoles were studied. Methods for the preparation of previously undescribed mononitro-substituted 1,3-benzothiazoles (4-nitro-2-(pentafluorosulfanyl)-1,3-benzothiazole, 4nitro-2-(trifluoromethyl)-1,3-benzothazole, and 6-nitro-2-(pentafluorosulfanyl)-1,3-benzothiazole) as well as a new method for the synthesis of the previously known 6-nitro-2-(trifluoromethyl)-1,3-benzothiazole were developed. The procedure involved the reaction of 2(trifluoromethyl)-1,3-benzothiazole with NH₄NO₃ in TFAA at room temperature. An efficient method for the preparation of 2substituted 4,5,6,7-tetrabromo-1,3-benzothiazoles based on the reaction of 2-substituted 1,3-benzothiazoles with NBS in TFA–H₂SO₄ at room temperature was proposed.