Water → 3-Nitrophenethyl methanesulfonate

Participants

Reaction Steps

A solution of 2-(3-nitrophenyl)ethanol (9 g, 53.8 mmol) in DCM (100 mL) was cooled to 0° C., then pyridine (22.7 g, 287 mmol) was dropwise added to the reaction solution. Then methylsulfonylchloride was added slowly dropwise, followed by stirring at room temperature for one hour. Water was added to terminate the reaction. The aqueous layer was extracted by ethyl acetate 3 times. The combined organic phase was washed with brine, dried over sodium sulfate and concentrated to give 3-nitrophenethyl methanesulfonate (13 g, yield 98%). 1H NMR: 400 MHz CDCl3 δ 8.13-8.10 (m, 2H), 7.60-7.53 (m, 1H), 7.53-7.47 (m, 1H), 4.48-4.45 (m, 2H), 3.19-3.15 (m, 2H), 2.95 (s, 3H).

Provenance & Evidence