Methanesulfonyl chloride → N-(3-(chloromethyl)phenyl)acetamide

Participants

Reaction Steps

Methanesulphonyl chloride (0.15 ml) was added to a stirred solution of 3-acetylaminobenzylalcohol (260 mg) and TEA (0.26 ml) in DCM (2 ml) at 0° C. The reaction was allowed to warm to room temperature and stirred for two hours. The mixture was diluted with EtOAc (20 mL) and MeOH (1 ml) and stirred for 5 minutes. The mixture was then washed with water (30 ml), organic layer was dried over sodium sulphate and solvent evaporated. The residue was columned on silica gel using DCM then ethyl acetate as eluant to give 3-acetylaminobenzylchloride (210 mg). 1H NMR (CDCl3) δ: 7.59 (s, 1H), 7.41 (d, 1H), 7.31 (t, 1H), 7.14 (d, 1H), 4.56 (s, 2H), 2.18 (s, 3H).

Provenance & Evidence