Triphenylphosphine → ((4'-Chlorobiphenyl-2-yl)methyl)triphenylphosphonium iodide

HRID 2406242Notes

Reaction equation

HRID 2406242 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:14][I:15])=[CH:4][CH:3]=1.[C:16]1([P:22]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1(C)C=CC=CC=1>[I-:15].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:14][P+:22]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 670542934'-Chloro-2-(iodomethyl)biphenyl

Product 1

HCID 86667196((4'-Chlorobiphenyl-2-yl)methyl)triphenylphosphonium iodideYield 93%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 4′-chloro-2-(iodomethyl)biphenyl in toluene (11 mL), triphenylphosphine (1.20 g, 4.57 mmol) was added. The result mixture was refluxed overnight, allowed to cool to room temperature and filtered. The solid was washed with ether and dried under vacuum to afford ((4′-Chlorobiphenyl-2-yl)methyl)triphenylphosphonium iodide (2.50 g, 93%): 1H NMR (400 MHz, chloroform-d) δ ppm 6.35-8.06 (m, 23 H), 5.12-5.63 (m, 2 H).

Workup

  1. temperatureThe result mixture was refluxed overnight
  2. filtrationfiltered
  3. washThe solid was washed with ether
  4. customdried under vacuum

Sources & evidence

ORD record
ord-08d64b8a1aa845e3ad194082dcb816ee
Source dataset
uspto-grants-2014_08
Patent number
US08809352B2

Reaction notes

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