Triphenylphosphine → HCID 86649984, compound

HRID 1892477Notes

Reaction equation

HRID 1892477 reaction equation
[Br:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[C:5]([F:12])[CH:4]=1.[C:13]1([P:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1(C)C=CC=CC=1>[Br-:1].[C:7]([C:6]1[CH:10]=[CH:11][C:3]([CH2:2][P+:19]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[CH:4][C:5]=1[F:12])([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 185102704-(Bromomethyl)-2-fluorobenzoic acid

Product 1

HCID 86649984HCID 86649984, compoundYield 105.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of 4-(bromomethyl)-2-fluorobenzoic acid (914.2 mg, 3.923 mmol) in toluene (20 ml) was added triphenylphosphine (1.029 g, 3.923 mmol). After heating the mixture under reflux for 6 hr, the reaction mixture was cooled to room temperature. The precipitate was collected by filtration, and dried under reduced pressure to give (4-carboxy-3-fluorobenzyl)(triphenyl)phosphoniumbromide (2.057 g, quantitative) as a white solid.

Workup

  1. temperatureAfter heating the mixture
  2. temperatureunder reflux for 6 hr
  3. filtrationThe precipitate was collected by filtration
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-9ed11a4635a24cd79fc00d1454152ab3
Source dataset
uspto-grants-2013_08
Patent number
US08507690B2

Reaction notes

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