4-Toluenesulfonyl chloride → 2,2-Difluoroethyl (4-methylphenyl)sulphonate

Participants

Reaction Steps

To a solution of p-toluensulfonyl chloride (7.0 g, 36.7 mmol) and 2,2-difluoroethanol 25a (2.00 g, 24.3 mmol, purchased from Linkchemical Co., Ltd) in dichloromethane (20 mL) was added triethylamine (10.2 mL, 73.1 mmol) at room temperature. The mixture was stirred at room temperature for 12 hours. The reaction mixture was adjusted with saturated aqueous ammonium chloride to pH 7 and washed with water (10 mL×2). The organic layer was washed with saturated aqueous sodium chloride (10 mL×2), dried over anhydrous sodium sulfate and filtered. The filtrated was concentrated in vacuo and the residue was purified by silica gel chromatography eluted with PE/EtOAc(v/v)=20/1 to give the title compound 25b as light yellow oil (3.4 g, 59.0%). The compound was characterized by the following spectroscopic data: 1H NMR (400 MHz, CDCl3) δ(ppm): 7.82 (d, 2H), 7.40 (d, 2H), 5.93 (m 1H), 4.18 (m, 2H), 2.47 (s, 3H).

Provenance & Evidence