Triphenylphosphine → 2-Ethoxycarbonylbenzyltriphenylphosphonium bromide

HRID 487676Notes

Reaction equation

HRID 487676 reaction equation
[Br:1][CH2:2][C:3]1[CH:13]=[CH:12][CH:11]=[CH:10][C:4]=1[C:5]([O:7][CH2:8][CH3:9])=[O:6].[C:14]1([P:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>O1CCCC1>[Br-:1].[CH2:8]([O:7][C:5]([C:4]1[CH:10]=[CH:11][CH:12]=[CH:13][C:3]=1[CH2:2][P+:20]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:6])[CH3:9]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 11032082Ethyl 2-(bromomethyl)benzoate

Product 1

HCID 190927132-Ethoxycarbonylbenzyltriphenylphosphonium bromideYield 56.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 2-bromomethylbenzoate (1.00 g) in tetrahydrofuran (10.0 ml) and triphenylphosphine (1.21 g) was heated under reflux for 8 hours. After being cooled, the resulting precipitates were collected by filtration and washed with tetrahydrofuran to give 2-ethoxycarbonylbenzyltriphenylphosphonium bromide (1.17 g).

Workup

  1. temperatureunder reflux for 8 hours
  2. temperatureAfter being cooled
  3. customthe resulting precipitates
  4. filtrationwere collected by filtration
  5. washwashed with tetrahydrofuran

Sources & evidence

ORD record
ord-caadd55a9c05445a9d4d5c1995bbf7ed
Source dataset
uspto-grants-1994_03
Patent number
US05296495

Reaction notes

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