4-Methylbenzoyl Chloride → 1-(1-Benzenesulfonyl-1H-pyrrol-3-yl)-1-p-tolyl-methanone

Participants

Reaction Steps

A solution of p-toluoyl chloride (4.91 g, 31.8 mmol) in ethylene dichloride (5 ml) was added to a suspension of aluminum chloride (4.62 g, 34.7 mmol) in ethylene dichloride (5 ml) in a 10 minutes period under an atmosphere of nitrogen. After 30 minutes thereto was added a solution of 1-benzenesulfonyl-1H-pyrrole (6.00 g, 28.9 mmol) in ethylene dichloride in a 10 minutes period and the mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into ice-water and the aqueous layer was extracted with dicloromethane twice. The organic layers were combined, dried and filtered. The filtrate was concentrated and the residue was purified with silica gel chromatography to give the subject compound (9.9 g, 100%).

Provenance & Evidence