Hydrochloric Acid → 2-(2-Naphthyloxy)ethyl 4-Bromobenzenesulfonate

Participants

Reaction Steps

To a solution of 2-(2-naphthyloxy)-1-ethanol (1.5 g, 7.97 mmol) and triethylamine (1.21 g, 11.95 mmol) in dichloromethane (20 mL) at 0° C. was added 4-bromobenzenesulfonyl chloride (2.12 g, 8.36 mmol) in dichloromethane (10 mL) dropwise over 30 minutes. The reaction was then warmed to room temperature and stirred for 16 hours before more 4-bromobenzenesulfonyl chloride (0.20 g, 0.80 mmol) was added and stirring was continued for 2 hours. The mixture was then poured into water (50 mL) and acidified with 2N aqueous hydrochloric acid (15 mL). The aqueous layer was extracted with dichloromethane and the combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to give a crude residue. This was purified by column chromatography on silica gel (50 g), eluting with hexane:ethyl acetate (9:2), to give the title compound (0.56 g, 17%) as a white crystalline solid.

Provenance & Evidence