Triphenylphosphine → (3-Carboxypropyl)(triphenyl)phosphanium bromide

HRID 2372904Notes

Reaction equation

HRID 2372904 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][C:5]([OH:7])=[O:6].[C:8]1([P:14]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>>[Br-:1].[C:5]([CH2:4][CH2:3][CH2:2][P+:14]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)([OH:7])=[O:6]

Participants

3

Reactant 2

HCID 11776TriphenylphosphineHCID 758094-Bromobutyric acid

Product 1

HCID 10717451(3-Carboxypropyl)(triphenyl)phosphanium bromide

Procedure

A solid mixture of 4-bromobutyric acid (100 g, 0.60 mol) and triphenylphosphine (157.1 g, 0.60 mol) was reacted at 140° C. (oil bath temperature) under argon for 3 hours. When heat was first applied, both solid starting materials melted to form a homogeneous solution. After a few minutes of heating, extensive precipitation occurred. After cooling to room temperature, a rock-hard solid was broken up, suspended in 250 mL of refluxing chloroform under argon, and diluted with 800 mL of ether. Stirring at room temperature was carried out for 30 minutes. The suspension was cooled to 0° C. (ice bath temperature), and the product was collected by filtration and washed with ether. Yield: 218.12 g.

Workup

  1. customwas reacted at 140° C. (oil bath temperature) under argon for 3 hours
  2. temperatureWhen heat
  3. customto form a homogeneous solution
  4. temperatureAfter a few minutes of heating
  5. customextensive precipitation
  6. additiondiluted with 800 mL of ether
  7. temperatureThe suspension was cooled to 0° C. (ice bath temperature)
  8. filtrationthe product was collected by filtration
  9. washwashed with ether

Sources & evidence

ORD record
ord-3829a20be94f40df98d9053a8935086d
Source dataset
uspto-grants-1992_03
Patent number
US05100889

Reaction notes

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