Hydrochloric Acid → 2,2-Difluoroethyl (4-methylphenyl)sulphonate

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Reaction Steps

To a solution of compound 2,2-difluoroethanol (1 g, 12.2 mmol) in CH2Cl2 (15 mL) was added TsCl (3.5 g, 18.3 mmol) at 0° C. The mixture was stirred at room temperature overnight. Then aqueous HCl was added to the mixture to adjusted the mixture to pH<7 and the mixture was separated. The aqueous phase was extracted with EtOAc and the combined organic phases was washed with brine, dried over Na2SO4 and concentrated in vacuo. The resulting residue was purified using column chromatography (petroleum ether:EtOAc=15:1) to provide 2,2-difluoroethyl 4-methylbenzenesulfonate. (2.5 g, yield: 86.8%). 1H-NMR (CDCl3, 400 MHz) δ 7.78 (d, J=8.0 Hz, 2H), 7.35 (d, J=8.0 Hz, 2H), 5.75˜6.04 (m, 1H), 4.10˜4.18 (m, 2H), 2.44 (s, 3H). MS (M+H)+: 267.

Provenance & Evidence