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

HRID 465866Notes

Reaction equation

HRID 465866 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>C(Cl)(Cl)Cl.C(OCC)C>[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

5

Reactant 2

HCID 11776TriphenylphosphineHCID 758094-Bromobutyric acid

Product 1

HCID 10717451(3-Carboxypropyl)(triphenyl)phosphanium bromideYield 93.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6212ChloroformSolvent

Procedure

A mixture of 100 g (599 mmol, Aldrich) of 4-bromobutyric acid and 157 g (599 mmol, Aldrich) of triphenylphosphine was heated to 130° for 2 hours. The reaction was cooled to room temperature. The resulting solid was solubilized in 250 mL of hot chloroform then diluted with 200 mL of diethyl ether. The mixture was cooled to room temperature then 0°. The solid which formed was collected by filtration and then dried under vacuum to afford 240 g (559 mmol, 93%) of title compound.

Workup

  1. temperaturewas heated to 130° for 2 hours
  2. temperatureThe mixture was cooled to room temperature
  3. custom0°
  4. customThe solid which formed
  5. filtrationwas collected by filtration
  6. customdried under vacuum

Sources & evidence

ORD record
ord-2306c0700bc04e1bb59fc6ecb9d37669
Source dataset
uspto-grants-1992_10
Patent number
US05153327

Reaction notes

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