Triphenylphosphonium hydrobromide → {5-Fluoro-2-[2-(4-trifluoromethylphenyl)ethoxy]benzyl}triphenylphosphonium bromide

HRID 1672655Notes

Reaction equation

HRID 1672655 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)=[C:6]([CH2:8]O)[CH:7]=1.[BrH:23].[C:24]1([PH+:30]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(#N)C>[Br-:23].[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)=[C:6]([CH:7]=1)[CH2:8][P+:30]([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 22178555Triphenylphosphonium hydrobromideHCID 578644135-Fluoro-2-[2-(4-trifluoromethylphenyl)ethoxy]benzyl alcohol

Product 1

HCID 86634291{5-Fluoro-2-[2-(4-trifluoromethylphenyl)ethoxy]benzyl}triphenylphosphonium bromideYield 82.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.7 g (5.41 mmol) of {5-fluoro-2-[2-(4-trifluoromethylphenyl)ethoxy]phenyl}methanol and 1.76 g (5.14 mmol) of triphenylphosphonium hydrobromide are heated under reflux in 20 ml of acetonitrile for three hours. A first product fraction is crystallized at −20° C. The mother liquor is concentrated, the residue is dissolved in dichloromethane, and a second fraction is crystallized with diethyl ether. A total of 2.71 g (76% yield) of the title compound is obtained.

Workup

  1. customA first product fraction is crystallized at −20° C
  2. concentrationThe mother liquor is concentrated
  3. dissolutionthe residue is dissolved in dichloromethane
  4. customa second fraction is crystallized with diethyl ether

Sources & evidence

ORD record
ord-25124effb83040bf96eac9300a88a2d8
Source dataset
uspto-grants-2011_08
Patent number
US07998988B2

Reaction notes

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