Triphenylphosphine → 4-(4-Fluorophenethyl)-3-methoxycarbonylbenzyl triphenylphosphonium bromide

HRID 2228029Notes

Reaction equation

HRID 2228029 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][CH2:7][C:8]2[CH:17]=[CH:16][C:15]([CH2:18][Br:19])=[CH:14][C:9]=2[C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.[C:22]1([P:28]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1(C)C=CC=CC=1>[Br-:19].[CH3:13][O:12][C:10]([C:9]1[CH:14]=[C:15]([CH:16]=[CH:17][C:8]=1[CH2:7][CH2:6][C:5]1[CH:20]=[CH:21][C:2]([F:1])=[CH:3][CH:4]=1)[CH2:18][P+:28]([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:11]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 18474623Methyl 2-(4-fluorophenethyl)-5-bromomethylbenzoate

Product 1

HCID 865903414-(4-Fluorophenethyl)-3-methoxycarbonylbenzyl triphenylphosphonium bromideYield 96%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of methyl 2-(4-fluorophenethyl)-5-bromomethylbenzoate (2.5 g; 7.1 mmol) and triphenylphosphine (2.1 g; 7.9 mmol) in toluene (50 ml) was heated at reflux for 3 hours. The solvent was evaporated and the residue was triturated in diethyl ether, filtered and washed three times with diethylether to give 3-methoxycarbonyl-4-[2-(4-fluorophenyl)ethyl]benzyl triphenylphosphonium bromide as a white solid. Yield=96%.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. customThe solvent was evaporated
  4. customthe residue was triturated in diethyl ether
  5. filtrationfiltered
  6. washwashed three times with diethylether

Sources & evidence

ORD record
ord-867fe6db3e534c18a6edb1ae92266503
Source dataset
uspto-grants-2002_07
Patent number
US06414145B1

Reaction notes

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