Triphenylphosphine → (2-Oxo-4-phenylbut-3-en-1-yl)(triphenyl)phosphanium bromide

HRID 2215884Notes

Reaction equation

HRID 2215884 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.[CH:20]([C:28]([CH2:30][Br:31])=[O:29])=[CH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1COCC1>[Br-:31].[C:14]1([P+:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:30][C:28](=[O:29])[CH:20]=[CH:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 54027402HCID 54027402, compound

Product 1

HCID 71374158(2-Oxo-4-phenylbut-3-en-1-yl)(triphenyl)phosphanium bromideYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a refluxed solution of triphenylphosphine (5.84 g, 22.3 mmol) in dry THF (25 mL) under nitrogen is slowly added bromomethyl styryl ketone (5.0 g, 22.3 mmol, in 25 ml THF). The reaction mixture is refluxed for 2 hrs. After cooling, the white precipitate is collected by filtration and washed with Et2O. Crystallization of the product with methanol gives triphenyl cinnamoylmethyl phosphonium bromide (9.3 g, 86%) as colorless needles, 1H NMR (400 MHz, DMSO-d6) d 8.02 (1H, d, J=16.0 Hz, β-CH═), 7.87, 7.76, 7.49 (20H, m, Ph), 7.00 (1H, d, J=16.0 Hz, a-CH═), 6.07 (2H, d, J=13.2 Hz CH2Br).

Workup

  1. temperatureThe reaction mixture is refluxed for 2 hrs
  2. temperatureAfter cooling
  3. filtrationthe white precipitate is collected by filtration
  4. washwashed with Et2O
  5. customCrystallization of the product with methanol

Sources & evidence

ORD record
ord-14d2e15ae3f64706830ab9eb47e7be09
Source dataset
uspto-grants-2006_09
Patent number
US07109380B2

Reaction notes

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