Ethanolamine → 4-bromo-N-(2-hydroxyethyl)benzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 4-bromo-benzenesulfonyl chloride (1.00 g, 3.92 mmol) in methylene chloride (25 mL) was added N,N-dimethylaminopyridine (0.608 g, 4.98 mmol). The reaction mixture was cooled to 0° C., and ethanolamine (0.287 g, 4.70 mmol) was added dropwise. After stirring for 30 minutes, the reaction mixture was quenched with water (15 mL). The resulting mixture was extracted with methylene chloride (3×25 mL). The combined organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product. Purification using silica gel chromatography (100-200 mesh, 10-15% ethyl acetate-hexane) provided 4-bromo-N-(2-hydroxy-ethyl)-benzenesulfonamide. MS calcd. for C8H11BrNO3S [(M+H)+] 281, obsd. 282.2.

Provenance & Evidence