Triphenylphosphine → HCID 86077235, compound

Participants

Reaction Steps

To a solution of nickel (II) bromide (dry under vacuum for 2 h at 140° C.) (3.6 g, 16 mmol, 0.5 equiv) in benzonitrile (dry overnight on activated 4 A molecular sieves) (250 mL) was added triphenylphosphine (26.0 g, 49 mmol, 3 equiv). The solution was heated under reflux for 15 min and then cooled to room temperature. (3-bromophenyl)diphenylphosphine (2) (11.1 g, 32.5 mmol, 1.0 equiv) in benzonitrile (20 mL plus rinse 5 mL) was added to the solution. The resulting solution was heated under reflux for 4 h then cooled to room temperature. A 10% (w/w) aqueous solution of potassium bromide (250 mL) was added. The layers were separated, and the aqueous layer was washed two times with CH2Cl2 (250 mL). The organic layer was washed three times with water (100 mL) and dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure. To the resulting solution was added hexane (750 mL) to precipitate the crude product. The precipitate was filtered and washed with hexane and then dissolved in CH2Cl2 (20 mL). Et2O (150 mL) was then added and the mixture was filtered. The resulting solid was purified by flash chromatography (MeOH/CH2Cl2, 0:100-10:90) to afford (3-diphenylphosphinophenyl)triphenylphosphonium bromide (3) (>95% purity) as a white solid (15.3 g, 78%), which was characterized as follows:

Provenance & Evidence