Chlorodiphenylphosphine → HCID 5017640, compound

Participants

Reaction Conditions

Reaction Steps

50 g (0.186 moles) of cyclopentadienylthallium (obtained from Fluka) were placed in a 500 ml flask together with 300 ml of diethyl ether. The suspension was cooled to 0° C. and 34.2 ml (0.186 moles) of diphenylchlorophosphine were added dropwise over 10 minutes. The suspension was then heated to room temperature, stirred for one hour and finally filtered through a frit. The solvent was then stripped off under vacuum to leave 39.5 g (85% of the theoretical yield) of the intermediate diphenylphosphinocyclopentadiene, compound 2. An 18.6 g portion (0.074 moles) of compound 2 was then diluted with toluene and cooled to 0° C. 33.2 ml of a 2.24 molar solution of butyllithium in hexane (0.074 moles) were added to this solution over 10 minutes. After being heated to room temperature and stirred for 2 hours, the yellow solution produced a precipitate, which was filtered off and washed with toluene and then with hexane. After drying under vacuum, 13.2 g of compound 3 (70% of the theoretical yield) were obtained in the form of a brownish powder (cf. J. Am. Chem. Soc. 105, (1983), 3882; Organometallics 1, (1982), 1591). 1H NMR (400 MHz, THF-d8): δ=7.3 (m, 4H); 7.15 (m, 6H); 5.96 (m, 2H); 5.92 (m, 2H); 31P NMR (161.9 MHz, THF-d8): δ=−20.

Provenance & Evidence