4-Toluenesulfonyl chloride → HCID 14606696, compound

Participants

Reaction Steps

A solution of 2-(4-bromophenyl)ethanol (3.48 mL, 24.87 mmol), p-toluenesulfonyl chloride (5.69 g, 29.8 mmol), and 4-(dimethylamino)pyridine (0.304 g, 2.487 mmol) in anhydrous dichloromethane (70 mL) was treated with triethylamine (6.93 mL, 49.7 mmol). The reaction stirred for 16 hours at ambient temperature. The reaction was diluted with ethyl acetate and washed with water and brine. The organic layer dried with sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel, eluting with a gradient of 10 to 20% ethyl acetate in hexanes, to give the title compound. MS ESI(+) m/z 356.9 [M+H]+.

Provenance & Evidence