Triphenylphosphine → 3-Methoxycarbonyl-5-phenylbenzyl triphenylphosphonium bromide

HRID 2228021Notes

Reaction equation

HRID 2228021 reaction equation
[Br:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7].[C:19]1([P:25]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1(C)C=CC=CC=1>[Br-:1].[CH3:9][O:8][C:6]([C:5]1[CH:4]=[C:3]([CH:12]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:10]=1)[CH2:2][P+:25]([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:7]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 18474535Methyl 3-bromomethyl-5-phenylbenzoate

Product 1

HCID 865903393-Methoxycarbonyl-5-phenylbenzyl triphenylphosphonium bromideYield 76%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of methyl 3-bromomethyl-5-phenylbenzoate (3.78 g; 1.23 mmol) and triphenyl phosphine (3.26 g; 1.23 mmol) in toluene (40 ml) was heated at reflux under argon atmosphere for 9 hours. The resulting solid was filtered, washed with ether and pentane to give 3-methoxycarbonyl-5-phenylbenzyl triphenylphosphonium bromide. Yield=76%.

Workup

  1. temperatureat reflux under argon atmosphere for 9 hours
  2. filtrationThe resulting solid was filtered
  3. washwashed with ether and pentane

Sources & evidence

ORD record
ord-25efba040565404b86d5917b94c698c3
Source dataset
uspto-grants-2002_07
Patent number
US06414145B1

Reaction notes

Loading…