3-((2,2,2- trifluoroethyl)thio)aniline

Uses

3-((2,2,2-trifluoroethyl)thio)aniline can be used as an intermediate in pharmaceutical research.

Synthesis

To a solution of 3-aminobenzenethiol (4.43 g, 35.4 mmol) in THF (225 mL) was added sodium hydride (1.77 g, 44.3 mmol) at 0 °C and stirred for 30 min. Then, 2,2,2-trifluoroethyl 4- methylbenzenesulfonate (9.0 g, 35.4 mmol) was added and the reaction mixture was stirred for 18 h. The reaction mixture was quenched with water (20 mL) and extracted with EtOAc (2x50 mL). The combined organic extracts were washed with water, dried over Na2SO4, fdtered, and concentrated under reduced pressure. The crude residue was purified by flash chromatography through a Redi-Sep pre-packed silica gel column, eluting with a gradient of 5 % to 10 % EtOAc in hexanes, to give 3-((2,2,2- trifluoroethyl)thio)aniline (5 g, 68 % yield) as a pale brown oil.