Methanesulfonyl chloride → 2-(Benzyloxy)phenyl methanesulfonate

Participants

Reaction Steps

2-(Benzyloxy)phenol (3.00 g, 14.98 mmol) was dissolved in dry DCM (70 mL) under nitrogen atmosphere and cooled on an ice-water bath. Methanesulfonyl chloride (2.06 g, 17.98 mmol) was added during stirring followed by TEA (2.27 g, 22.47 mmol). The reaction mixture was stirred at rt for 2 h and then washed with aqueous saturated NaHCO3, dried (MgSO4), filtered and evaporated affording the title compound (4.04 g, 96.9%). 1H NMR (500 MHz, CDCl3): δ 3.09 (s, 3H), 5.15 (s, 2H), 7.02 (dt, 1H), 7.09 (dd, 1H), 7.27 (dt, 1H), 7.34-7.48 (m, 6H); 13C NMR (125 MHz, CDCl3): δ 38.72, 71.37, 114.67, 121.79, 125.06, 127.95, 128.50, 128.68, 129.00, 136.20, 138.96, 150.91.

Provenance & Evidence