4-Toluenesulfonyl chloride → 3-Nitrophenethyl tosylate

Participants

Reaction Steps

A 500 mL round-bottomed flask was charged with 2-(3-nitrophenyl)ethanol (1.0235 g, 6.12 mmol), 4-dimethylaminopyridine (0.075 g, 0.612 mmol) and p-toluenesulfonyl chloride (1.401 g, 7.35 mmol) in CH2Cl2 (61.2 ml). Triethylamine (1.707 ml, 12.25 mmol) was added, and the mixture stirred at ambient temperature for 3 hours. The reaction mixture was washed with water and brine, dried (MgSO4), filtered and concentrated onto silica gel. The crude product was purified by flash chromatography using an Argonaut Flashmaster Solo 25 g column (100% hexanes to 30% ethyl acetate:hexanes over 25 minutes, then to 100% ethyl acetate over 10 minutes) to provide the title compound. MS (ESI(+)) m/e 338.9 (M+NH4)+.

Provenance & Evidence