Triphenylphosphine → [(3-Carboxyphenyl)methyl](triphenyl)phosphanium bromide

HRID 1892495Notes

Reaction equation

HRID 1892495 reaction equation
[Br:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7].[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>C(#N)C>[Br-:1].[C:6]([C:5]1[CH:4]=[C:3]([CH:11]=[CH:10][CH:9]=1)[CH2:2][P+:18]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)([OH:8])=[O:7]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 2456503-(Bromomethyl)benzoic acid

Product 1

HCID 19957492[(3-Carboxyphenyl)methyl](triphenyl)phosphanium bromideYield 82.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-(bromomethyl)benzoic acid (16.50 g, 76.73 mmol) in acetonitrile (76.7 ml) was added triphenylphosphine (22.14 g, 84.40 mmol). After heating the mixture under reflux for 2 hr, the reaction mixture was cooled to room temperature. The precipitate was collected by filtration and dried under reduced pressure to give (3-carboxybenzyl)(triphenyl)phosphoniumbromide (30.13 g, 63.12 mmol, yield 82.3%) as a white solid.

Workup

  1. temperatureAfter heating the mixture
  2. temperatureunder reflux for 2 hr
  3. filtrationThe precipitate was collected by filtration
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-bbac79a1f17e40f2b9249410567ec8fe
Source dataset
uspto-grants-2013_08
Patent number
US08507690B2

Reaction notes

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