Boron trifluoride etherate → (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-diethyl ether (350 g, 2.47 mol) under an atmosphere of nitrogen. The mixture was allowed to stand at room temperature for 7 days. The reaction solution was washed with 1N hydrochloric acid (750 ml) twice, an aqueous 1N sodium hydroxide solution (750 ml) and a saturated aqueous sodium chloride solution (100 ml) in the order, dried and filtered. The filtrate was further concentrated to about 500 ml at atmospheric pressure, followed by addition of hexane (500 ml). Further the solution was concentrated to about 500 ml and cooled to 10° C. The precipitate was filtered, washed with hexane and toluene in the order, and dried to give the subject compound (315 g, 71%).

Provenance & Evidence