Triphenylphosphine → (2-Bromophenethyl)triphenylphosphonium iodide

HRID 921101Notes

Reaction equation

HRID 921101 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][I:10].[C:11]1([P:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C1(C)C=CC=CC=1>[I-:10].[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][P+:17]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 109358371-Bromo-2-(2-iodoethyl)benzene

Product 1

HCID 118307054(2-Bromophenethyl)triphenylphosphonium iodideYield 76%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 1-bromo-2-(2-iodoethyl)benzene (0.3244 g, 1.043 mmol) in toluene (1.739 ml) in a pressure tube was added triphenylphosphine (0.274 g, 1.043 mmol) and the tube was sealed and stirred at 100° C. The mixture was cooled to room temperature. The product solidified and the solvent was decanted off. The solid was taken up in DCM and concentrated to give the title compound (0.4526 g, 0.790 mmol, 76% yield) as a white foam. LCMS (M+H) calcd for C26H24BrP: 447.07. found: 448.0.

Workup

  1. customthe tube was sealed
  2. temperatureThe mixture was cooled to room temperature
  3. customthe solvent was decanted off
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e6ea448679d74201b78033a71cb153ac
Source dataset
uspto-grants-2016_03
Patent number
US09273067B2

Reaction notes

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