1,4-Dibromobutane → 1-(4-Bromobutyl)pyrrolidin-2-one

Participants

Reaction Steps

To a suspension of 37 g of powdered KOH in 500 ml of tetrahydrofuran (THF) were added 25.2 g of tetraethylammonium bromide. Then, a solution of 51.6 g of 2-pyrrolidinone and 129.6 g of 1,4-dibromobutane in 100 ml of THF was added dropwise to the mixture. The mixture was heated and refluxed for 2 hours. The precipitate was filtered, and the THF evaporated. The residue was dissolved in dichloromethane, washed with water, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue distilled to yield 51.2 g of 1-(4-bromobutyl)-2-pyrrolidinone (38.8% yield) having a boiling point of 120° C. at 0.05 mm Hg.

Provenance & Evidence