Chlorodiphenylphosphine → HCID 5017640, compound

HRID 634874Notes

Reaction equation

[CH:1]1([Tl])[CH:5]=[CH:4][CH:3]=[CH:2]1.[C:7]1([P:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)Cl)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(OCC)C>[C:15]1([P:13]([C:2]2[CH2:1][CH:5]=[CH:4][CH:3]=2)[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

Conditions

Temperature: 0 °C

Procedure

50 g (0.186 mol) of cylopentadienyl-thallium (obtained from Fluka) together with 300 ml of diethyl ether were placed in a 500 ml flask. The slurry was cooled to 0° C. and 34.2 ml (0.186 mol) of diphenylchlorophosphine were added dropwise over a period of 10 minutes. The slurry was then warmed to room temperature, stirred for one hour and finally filtered through a frit. The solvent was then taken off under reduced pressure and left 39.5 g (85% of the theoretical yield) of the intermediate diphenylphosphino-cyclopentadiene, Compound 5. 18.6 g (0.074 mol) of Compound 5 were then diluted with toluene and cooled to 0° C. 33.2 ml of a 2.24 molar solution of butyl-lithium in hexane (0.074 mol) were added to the above solution over a period of 10 minutes. After warming to room temperature and stirring for 2 hours, the yellow solution gave a precipitate which was filtered off and washed with toluene and subsequently with hexane. Drying under reduced pressure gave 13.2 g of Compound 6 (70% of the theoretical yield) as a brownish powder (cf. J. Am. Chem. Soc. 105 (1983); 3882; Organometallics 1 (1982), 1591).

Workup

temperatureThe slurry was then warmed to room temperature
filtrationfinally filtered through a frit
waitleft 39.5 g (85% of the

Sources & evidence

ORD record: ord-b2fcf8f9a060412389b64970e687f90f
Source dataset: uspto-grants-2001_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06184320B2

Reaction notes

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