Water → (Benzyloxy)ethyl 4-bromobenzenesulfonate

Participants

Reaction Steps

A solution of 4-bromobenzenesulfonyl chloride (5.5 g, 21.7 mmol) dissolved in dichloromethane (15 ml) was added dropwise to a solution of 2-benzyloxyethanol (3.0 g, 19.7 mmol) in triethylamine (3 g, 29.6 mmol) at 0° C. under nitrogen. The resultant mixture was stirred for 16 h at room temperature. To the reaction mixture was added water (3 ml) and then the combined mixture was poured onto water (100 ml) and the product was extracted with dichloromethane. The organic layer was washed repeatedly with water and then saturated aqueous sodium hydrogen carbonate solution, before drying (Na2SO4) and concentrating in vacuo to give the title compound as a white solid (6.9 g, 94%).

Provenance & Evidence