Triphenylphosphine → (4-Carboxybenzyl)triphenylphosphonium bromide

HRID 970249Notes

Reaction equation

HRID 970249 reaction equation
[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([OH:11])=[O:10])=[CH:5][CH:4]=1.[C:12]1([P:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1(C)C=CC=CC=1>[Br-:1].[C:9]([C:6]1[CH:7]=[CH:8][C:3]([CH2:2][P+:18]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH:4][CH:5]=1)([OH:11])=[O:10]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 225994-(Bromomethyl)benzoic acid

Product 1

HCID 22675580(4-Carboxybenzyl)triphenylphosphonium bromideYield 94.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
115 °C

Procedure

10.7 g (50 mmole) of α-bromo-4-toluoic acid and 13.1 g (50 mmole) of triphenylphosphine were dissolved in 105 ml of toluene under a nitrogen atmosphere. The mixture was heated at 115° C. for 5 hours. After cooling, the mixture was filtered and dried in a vacuum-oven at 60° C. and 22.6 g of a white solid were obtained (yield 94.5%).

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered
  3. customdried in a vacuum-oven at 60° C.

Sources & evidence

ORD record
ord-30597f77bce64bb1a274e6cab44ddfc2
Source dataset
uspto-grants-2007_12
Patent number
US07311948B2

Reaction notes

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