Benzyl Alcohol → 1-(Phenoxymethyl)-2-sulfamoylbenzene

Participants

Reaction Conditions

Reaction Steps

To a solution of benzyl alcohol (1 g, 8.6 mmol) in 10 mL of dry DMF was added to NaH (0.7 g, 17.1 mmol.) at 0° C. The reaction mixture was stirred at 0° C. for 30 min under N2. To the resulting mixture was added 2-sulfamoyl fluorobenzene (1 g, 5.7 mmol.) in 20 mL of dry DMF. The reaction mixture was stirred at 80-90° C. for 3 hours. After cooling to r.t., the reaction mixture was poured into ice-water and neutralized with aq. HCl (2 M) to pH 7. The mixture was extracted with ethyl acetate (3×50 mL). The combined organic layer was over Na2SO4, filtered and concentrated to afford crude 1-(phenoxymethyl)-2-sulfamoylbenzene (1 g, 66.7%), which was used directly without further purification.

Provenance & Evidence