Triphenylphosphine → 2-{3-[3-(4-Fluorophenoxy)propoxy]phenyl}-ethyl triphenylphosphonium bromide

HRID 467346Notes

Reaction equation

HRID 467346 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:12]=[C:13]([CH2:17][CH2:18][Br:19])[CH:14]=[CH:15][CH:16]=2)=[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>C(O)C>[Br-:19].[F:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:12]=[C:13]([CH2:17][CH2:18][P+:28]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:14]=[CH:15][CH:16]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 197557082-{3-[3-(4-Fluorophenoxy)propoxy]phenyl}-ethyl bromide

Product 1

HCID 867450082-{3-[3-(4-Fluorophenoxy)propoxy]phenyl}-ethyl triphenylphosphonium bromideYield 50%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 20 mmol of bromide (example 141) and 30 mmol of triphenyl phosphine in 60 ml of ethanol was refluxed 20 hours under nitrogen and then cooled and evaporated in vacuo. The residue was chromatographed on silica gel using first CHCl3 to elute starting material residues and then 5% CH3OH in CHCl3 to elute the product. Evaporation of pure fractions yielded the title compound as a viscous oil.

Workup

  1. temperaturecooled
  2. customevaporated in vacuo
  3. customThe residue was chromatographed on silica gel using first CHCl3
  4. washto elute
  5. wash5% CH3OH in CHCl3 to elute the product
  6. customEvaporation of pure fractions

Sources & evidence

ORD record
ord-234f14db61f24964b55ead5bb561f661
Source dataset
uspto-grants-1992_10
Patent number
US05159097

Reaction notes

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