Triphenylphosphine → Phosphonium, [[3-(methoxycarbonyl)phenyl]methyl]triphenyl-, bromide

HRID 2074297Notes

Reaction equation

HRID 2074297 reaction equation
[C:1]1([P:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:20][CH2:21][C:22]1[CH:23]=[C:24]([CH:29]=[CH:30][CH:31]=1)[C:25]([O:27][CH3:28])=[O:26]>>[Br-:20].[CH3:28][O:27][C:25]([C:24]1[CH:23]=[C:22]([CH:31]=[CH:30][CH:29]=1)[CH2:21][P+:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:26]

Participants

3

Reactant 2

HCID 11776TriphenylphosphineHCID 517981Methyl 3-(bromomethyl)benzoate

Product 1

HCID 10051285Phosphonium, [[3-(methoxycarbonyl)phenyl]methyl]triphenyl-, bromideYield 100.3%

Conditions

Temperature
80 °C

Procedure

Triphenylphosphine (85.8 g) was added to a Tol (400 ml) solution of methyl 3-bromomethylbenzoate (50.0 g), followed by stirring at 80° C. for 10 hours. After this was cooled to room temperature, the crystal precipitated was collected by filtration and washed with Tol. This was dried under reduced pressure to obtain (3-methoxycarbonylbenzyl)(triphenyl)phosphonium bromide (107.6 g).

Workup

  1. temperatureAfter this was cooled to room temperature
  2. customthe crystal precipitated
  3. filtrationwas collected by filtration
  4. washwashed with Tol
  5. customThis was dried under reduced pressure

Sources & evidence

ORD record
ord-e3110e3ac0ff4a3d956f2b58fff5ee6d
Source dataset
uspto-grants-2011_04
Patent number
US07919495B2

Reaction notes

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