4-Toluenesulfonyl chloride → HCID 24805800, compound

Participants

Reaction Steps

Treat a solution of (1-(trifluoromethyl)cyclopropyl)methanol (7 g, 50 mmol) and 4-methylbenzene-1-sulfonyl chloride (10.4 g, 55 mmol) in anhydrous DCM (100 mL) with TEA (10 g, 100 mmol) and N,N-dimethylpyridin-4-amine (0.6 g, 5 mmol). Stir at RT overnight. Wash the mixture successively with HCl (2M), saturated NaHCO3, and brine, dry over Na2SO4 and concentrate under reduced pressure to give the title compound (12 g, 81% yield). 1H NMR (400 MHz, DMSO-d6): δ 7.79 (d, J=8.0 Hz, 2H), 7.50 (d, J=8.0 Hz, 2H), 4.13 (s, 2H), 2.43 (s, 3H), 1.08-1.05 (m, 2H), 0.96-0.94 (m, 2H).

Provenance & Evidence