Triphenylphosphine → (3-Carboxypropyl)(triphenyl)phosphanium bromide

Participants

Reaction Steps

A solid mixture of 4-bromobutyric acid (100 g, 0.60 mol) and triphenylphosphine (157.1 g, 0.60 mol) was reacted at 140° C. (oil bath temperature) under argon for 3 hours. When heat was first applied, both solid starting materials melted to form a homogeneous solution. After a few minutes of heating, extensive precipitation occurred. After cooling to room temperature, a rock-hard solid was broken up, suspended in 250 mL of refluxing chloroform under argon, and diluted with 800 mL of ether. Stirring at room temperature was carried out for 30 minutes. The suspension was cooled to 0° C. (ice bath temperature), and the product was collected by filtration and washed with ether. Yield: 218.12 g.

Provenance & Evidence