4-(Trifluoromethylthio)aniline

403-66-7

372-16-7

General procedure for the synthesis of 4-((trifluoromethyl)thio)aniline from 4-trifluoromethylthio nitrobenzene: A palladium-carbon catalyst (10% Pd/C, 3.5 g) was added to a solution of 4-nitrophenyl trifluoromethyl sulfide (33.5 g, 0.15 mol) in ethanol (400 mL). The reaction mixture was placed in an autoclave and hydrogenated in a hydrogen atmosphere at 40 atm at room temperature for 8 hours. Upon completion of the reaction, the mixture was filtered through a diatomaceous earth pad and the filter cake was washed well with ethanol. The filtrate and washings were combined and concentrated under reduced pressure to remove the solvent. The residue was washed with water to give 28.4 g (98% yield) of 4-aminophenyl trifluoromethyl sulfide as a brown liquid. The product was characterized as follows: melting point: 110-112 °C/1.70 KPa (literature value: b.p. 113 °C/1.73 KPa); 1H NMR (300 MHz, CDCl3) δ 7.62 (d, J = 8.30 Hz, 2H), 7.42 (dd, J = 8.30 Hz, J = 1.90 Hz, 2H), 3.84 (s, 2H NH2); 19F NMR (220 MHz, CDCl3) δ 44.5 (s, 3F, SCF3); 13C NMR (75 MHz, CDCl3) δ 149.1, 138.2, 126.7, 115.3, 111.3.