4-Methylbenzoyl Chloride → (1-benzenesulfonyl-1H-pyrrol-2-yl)(4-methylphenyl)ketone

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-benzenesulfonyl-1H-pyrrole (284 g, 1.37 mol) in dichloromethane (1.0 L) were added p-toluoyl chloride (318 g, 2.06 mol) and boron trifluoride ether complex (350 g, 2.47 mol) in a stream of nitrogen and the mixture was allowed to stand for 7 hours at room temperature. The reaction mixture was washed with 1N aqueous hydrochloric acid solution (750 mL) twice, 1N aqueous sodium hydroxide solution (750 mL) and saturated brine (100 mL) successively, dried over magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure so that the volume became about 500 ml and thereto was added hexane (500 mL). Further the mixture was concentrated so that the volume became about 500 ml, and cooled to 10° C. and resulting crystals were collected by filtration. The crystals were washed with hexane and then toluene and dried to give the subject compound (315 g, 71%).

Provenance & Evidence