Triphenylphosphine → (5-Carboxypentyl)triphenylphosphanium bromide

HRID 1651212Notes

Reaction equation

HRID 1651212 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8].[C:10]1([P:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(Cl)(Cl)Cl.CCOCC>[Br-:1].[C:7]([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][P+:16]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)([OH:9])=[O:8]

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 202106-Bromohexanoic acid

Product 1

HCID 2779280(5-Carboxypentyl)triphenylphosphanium bromideYield 90.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6212ChloroformSolvent

Procedure

An intimate mixture of 6-bromohexanoic acid (19.5 g) and triphenylphosphine (26.3 g) was heated at 150° for three hours in a closed flask. After the reaction was cooled, the crude product was dissolved in chloroform (200 mL) and the resulting solution was diluted just to the cloud point with ether. The mixture was stored at 0° C. for several hours, then the solids were collected by filtration, washed with ether and dried in vacuo to yield 41.3 g of (5-carboxypentyl)triphenylphosphonium bromide, mp 197°-198° C. Anal. Calculated for C24H26BrO2P: C, 63.03; H, 5.73; Br, 17.47. Found: C, 63.00; H, 5.76; Br, 17.54.

Workup

  1. temperaturewas heated at 150° for three hours in a closed flask
  2. temperatureAfter the reaction was cooled
  3. waitThe mixture was stored at 0° C. for several hours
  4. filtrationthe solids were collected by filtration
  5. washwashed with ether
  6. customdried in vacuo

Sources & evidence

ORD record
ord-d330c6297c944efc8c7573db2be3f05d
Source dataset
uspto-grants-1990_05
Patent number
US04927838

Reaction notes

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