Triethylamine → Phenylphosphine

Participants

Reaction Steps

A one liter xylene solution containing iodobenzene (375 g, 1.84 moles), triethylamine (150 g, 1.5 moles) and the palladium dimer (1:1 adduct of palladium(II) acetate and tri(o-tolyl)phosphine, 1.20 g, 1.2 mmole, 0.07 mole %) was charged to a one gallon autoclave under a nitrogen blanket. The solution was maintained at 500 psig phosphine pressure and 110° C., with stirring at 500 rpm, for 5 hours. At this time the autoclave was cooled to ambient temperature, vented and discharged as described above. Analysis of the xylene phase by GC/FID (with area percent integration) gave only monophenylphosphine (9%) and diphenylphosphine (7%), with no sign of triphenyl-phosphine, for a total conversion of iodobenzene of approximately 16%.

Provenance & Evidence