Toluene → (7-Carboxyheptyl)triphenylphosphonium bromide

HRID 1158136Notes

Reaction equation

HRID 1158136 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]([OH:10])=[O:9].[CH:11]1[CH:16]=[CH:15][C:14]([P:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:13][CH:12]=1.[C:30]1(C)C=CC=CC=1>>[Br-:1].[C:8]([CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:30][P+:17]([C:14]1[CH:13]=[CH:12][CH:11]=[CH:16][CH:15]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([OH:10])=[O:9]

Participants

4

Reactant 3

HCID 1140TolueneHCID 11776TriphenylphosphineHCID 1217237-Bromoheptanoic acid

Product 1

HCID 11317723(7-Carboxyheptyl)triphenylphosphonium bromide

Procedure

A solution of 7-bromoheptanoic acid (5.000 g, 23.913 mmol) and PPh3 (6.899 g, 26.304 mmol) in 50 mL of toluene was refluxed for 63 h. After cooling to room temperature, the solvent was removed under reduced pressure and the residue was tritited with ether three times and dried in vacuum to give the title compound as a white foam solid (9.240 g, 82% yield).

Workup

  1. customthe solvent was removed under reduced pressure
  2. customdried in vacuum

Sources & evidence

ORD record
ord-c73c8d60dcba48aabfa517530d1343a3
Source dataset
uspto-grants-2010_10
Patent number
US07807720B2

Reaction notes

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