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

Participants

Reaction Conditions

Reaction Steps

Under nitrogen atmosphere, to a solution of 1-benzenesulfonyl-1H-pyrrole (283.9 g) in methylene chloride (1.0 L) were added p-toluoyl chloride (318 g) and boron trifluodie ether complex (350 g), and the mixture was allowed to stand at room temperature for 7 days. The reaction solution was washed twice with IN hydrochloric acid (750 mL), washed with 1N aqueous sodium hydroxide solution (750 mL) and a saturated brine (100 mL), dried, and filtered. The filtrate was concentrated to about a half volume thereof under atmospheric pressure, and thereto was added hexane (500 mL). The mixture was further concentrated, and methylene chloride was evaporated off. The resultant was cooled to 10° C., and the precipitated crystals were collected by filtration, washed with hexane and toluene, and dried to give (1-benzenesulfonyl-1H-pyrrol-2-yl) (4-methylphenyl) ketone (315 g, 71%).

Provenance & Evidence