Triphenylphosphine → (3-Ethoxy-3-oxopropyl)(triphenyl)phosphanium bromide

Participants

Reaction Steps

Ethyl 3-bromopropionate (1.81 g, 0.01 moles) was added to a three-necked, 100 mL round bottom flask equipped with a magnetic stirrer, thermocouple and temperature controller, condenser, and heating mantle. Triphenylphosphine (2.62 g, 0.01 moles) and toluene (25 ml) was added and the mixture was heated to reflux temperature. As the temperature turned 90° C., the mixture turned slightly cloudy. After 3 hours at 115° C., the reaction mixture was cooled to room temperature, during which time a yellow colored waxy material settled to the bottom of the reaction flask. The liquid was removed and the residual waxy solid dissolved in dichloromethane (about 10 ml). Diethyl ether (about 15 ml) was added to the dichloromethane solution and a precipitate was formed. The precipitate was collected by filtration and dried under vacuum to give the required phosphonium salt (0.8 grams; 18% yield). The structure of the product was confirmed by 1H NMR analysis.

Provenance & Evidence