Triphenylphosphine → (4-Chlorophenyl)(triphenyl)phosphanium iodide

HRID 443080Notes

Reaction equation

[C:1]1([P:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([I:27])=[CH:23][CH:22]=1>C1(C)C(C)=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[I-:27].[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([P+:7]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 150 °C

Procedure

In 100 mL-volume egg-plant type flask, 3.30 g (11.4 mmol.) of triphenylphosphine and 3.00 g (12.6 mmol.) of p-chloroiodobenzene were dissolved in 40 mL of xylene. To the solution was added 30.0 mg (0.134 mmol.) of palladium acetate, and the resulting mixture was stirred at 150° C. for 9.5 hours. After the reaction was complete, the reaction mixture was cooled to room temperature, and the precipitate was collected on a filter by suction. The collected precipitate was washed with xylene and dried under reduced pressure at 130° C. for 3 hours. There was obtained 5.48 g (yield: 87%) of p-chlorophenyltriphenylphosphonium iodide (m.p.: 219°-222° C., elemental analysis: found: C 57.84%, H 3.74%, calculated: C 57.57%, H 3.82%).

Workup

temperaturethe reaction mixture was cooled to room temperature
customthe precipitate was collected on
filtrationa filter by suction
washThe collected precipitate was washed with xylene
customdried under reduced pressure at 130° C. for 3 hours

Sources & evidence

ORD record: ord-11fb1821dca640c288530ca252f38387
Source dataset: uspto-grants-1999_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05892091

Reaction notes

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