Triphenylphosphine → (3-(Ethoxycarbonyl)propyl)triphenylphosphonium Bromide

HRID 726505Notes

Reaction equation

HRID 726505 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[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>C1(C)C=CC=CC=1>[Br-:1].[CH2:8]([O:7][C: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)=[O:6])[CH3:9]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 76300Ethyl 4-bromobutyrate

Product 1

HCID 2773643(3-(Ethoxycarbonyl)propyl)triphenylphosphonium BromideYield 73.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

First, 19.6 g of ethyl 4-bromobutyrate, 24.4 g of triphenylphosphine, and 70 ml of toluene were placed in a 200 ml flask. The mixture was stirred under reflux for 10 hours. After the mixture was cooled, produced crystal was recovered by filtration and washed with toluene to obtain 31.4 g of 3-ethoxycarbonylpropyltriphenylphosphonium bromide (Y: 68%). The compound thus obtained had an m.p. of 173° C. to 180° C.

Workup

  1. temperatureunder reflux for 10 hours
  2. temperatureAfter the mixture was cooled
  3. customproduced crystal
  4. filtrationwas recovered by filtration
  5. washwashed with toluene

Sources & evidence

ORD record
ord-d7e2ccf6d45f4462aa9df345bfab0ff4
Source dataset
uspto-grants-1998_01
Patent number
US05709911

Reaction notes

Loading…