Hydrochloric Acid → 1-Chloro-2-nitro-4-[(trifluoromethyl)thio]benzene

Participants

Reaction Steps

2-Nitro-4-trifluoromethylthioaniline (0.5 g) in dry acetonitrile (3 cm3) was added over 0.5 hr. with stirring to copper (II) chloride (0.34 g) and tert-butyl nitrite (0.32 g) in dry acetonitrile (5 cm3) at 60° C. After 1 hr. the reaction was cooled to ambient temperature, poured into water, acidified with hydrochloric acid and extracted with ethyl acetate. The organic phase was washed with water (3×50 cm3) dried (magnesium sulphate) and evaporated under reduced pressure to give the required product as an oil; M+ =257; 1H NMR (CDCl3): δ7.65(d 1H); 7.80(dd 1H); 8.20(d 1H).

Provenance & Evidence