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

HRID 2228009Notes

Reaction equation

HRID 2228009 reaction equation
[Br:1][CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[CH:4]=1.[C:20]1([P:26]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1(C)C=CC=CC=1>[Br-:1].[F:19][C:16]1[CH:17]=[CH:18][C:13]([C:5]2[CH:4]=[C:3]([CH:12]=[CH:11][C:6]=2[C:7]([O:9][CH3:10])=[O:8])[CH2:2][P+:26]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 18399506Methyl 4-bromomethyl-2-(4-fluorophenyl)benzoate

Product 1

HCID 865903363-(4-Fluorophenyl)-4-methoxycarbonylbenzyl triphenylphosphonium bromideYield 78%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of methyl 4-bromomethyl-2-(4-fluorophenyl)benzoate (12.85 g; 0.04 mol) and triphenyl phosphine (10.53 g; 0.04 mol) in toluene (230 ml) was treated at reflux for 3 hours. The resulting solid was filtered, washed with ether and pentane and dried to give 3-(4-fluorophenyl)-4-methoxycarbonylbenzyltriphenylphosphonium bromide (12.78 g, 78%).

Workup

  1. temperatureat reflux for 3 hours
  2. filtrationThe resulting solid was filtered
  3. washwashed with ether and pentane
  4. customdried

Sources & evidence

ORD record
ord-1a108f6073914610aa5bae101482aef9
Source dataset
uspto-grants-2002_07
Patent number
US06414145B1

Reaction notes

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