Toluene → (7-Carboxyheptyl)triphenylphosphonium bromide

HRID 885518Notes

Reaction equation

HRID 885518 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 tritiated 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-9891dc8941e14e369f695dc731b674ec
Source dataset
uspto-grants-2012_08
Patent number
US08242174B2

Reaction notes

Loading…