反应详情

A solution of 2-(p-chlorophenyl)-5-[(trifluoromethyl)thio]pyrrole (1.0 g, 0.0036 mol) in acetic acid is cooled with an ice bath, treated with nitric acid (0.24 g, 0.00378 mol), stirred for two hours, poured into ice-water and stirred for one hour. The aqueous solution is filtered and the filter cake is washed with water and dried in a vacuum dessicator to obtain a tan solid. Flash chromatography of the solid using silica gel and a 1:10 ethyl acetate/hexanes solution gives 2-(p-chlorophenyl)-3-nitro-5-[(trifluoromethyl)thio]pyrrole as a yellow solid (0.45 g, mp 143°-145° C.) and 5-(p-chlorophenyl)-3-nitro-2-[(trifluoromethyl)thio]pyrrole as a yellow solid (0.17 g, mp 185°-193° C.). Both products are identified by 1HNMR, 19FNMR and 13CNMR spectral analyses.

1. stirringstirred for one hour
2. filtrationThe aqueous solution is filtered
3. washthe filter cake is washed with water
4. customdried in a vacuum dessicator
5. customto obtain a tan solid