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

HRID 1089155Notes

Reaction equation

HRID 1089155 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.CCOCC>[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 93.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6212ChloroformSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 100 g of 4-bromobutyric acid and 156.9 g of triphenylphosphine was heated under argon at 130° C. for 2 hours. The cooled reaction mixture was suspended in 250 mL of chloroform and heated to reflux, then diluted with 200 mL of ether. This was stirred for 30 minutes at room temperature, chilled to 0° C, and filtered. The solid was dried in vacuo to afford 240 g title salt.

Workup

  1. customThe cooled reaction mixture
  2. temperatureheated
  3. temperatureto reflux
  4. temperaturechilled to 0° C
  5. filtrationfiltered
  6. customThe solid was dried in vacuo

Sources & evidence

ORD record
ord-0c9c8fd2204f4da2b24e0f3fa4091609
Source dataset
uspto-grants-1990_10
Patent number
US04965279

Reaction notes

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