Triphenylphosphine → [4-(Methoxycarbonyl)benzyl](triphenyl)phosphonium bromide

HRID 1866451Notes

Reaction equation

HRID 1866451 reaction equation
[Br:1][CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][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].[CH3:10][O:9][C:7]([C:6]1[CH:11]=[CH:12][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][CH:5]=1)=[O:8]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 256687Methyl 4-(bromomethyl)benzoate

Product 1

HCID 2764257[4-(Methoxycarbonyl)benzyl](triphenyl)phosphonium bromideYield 95.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of methyl 4-(bromomethyl)-benzoate (2.29 g, 10 mmol) and triphenylphosphine (2.62 g, 10 mmol) in toluene (40 mL) was refluxed for 2 hours and then cooled down to room temperature. The precipitate was filtered and dried under vacuum, giving 4.71 g (95%) of white solid.

Workup

  1. filtrationThe precipitate was filtered
  2. customdried under vacuum

Sources & evidence

ORD record
ord-2eac2d809ec44c079c3938e403c0cbd0
Source dataset
uspto-grants-2009_12
Patent number
US07629375B2

Reaction notes

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