(4-Bromo-2-fluorobenzyl)triphenylphosphonium bromide → 4-Bromo-2-fluoro-1-(2-methylprop-1-en-1-yl)benzene

HRID 1741839Notes

Reaction equation

HRID 1741839 reaction equation
[Br-].[Br:2][C:3]1[CH:28]=[CH:27][C:6]([CH2:7][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[C:5]([F:29])[CH:4]=1.[CH3:30][C:31](C)([O-])[CH3:32].[K+]>CC(C)=O>[Br:2][C:3]1[CH:28]=[CH:27][C:6]([CH:7]=[C:31]([CH3:32])[CH3:30])=[C:5]([F:29])[CH:4]=1

Participants

4

Reactant 2

HCID 11114149(4-Bromo-2-fluorobenzyl)triphenylphosphonium bromideHCID 23665647Potassium tert-butoxide

Product 1

HCID 190107454-Bromo-2-fluoro-1-(2-methylprop-1-en-1-yl)benzeneYield 43.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of (4-bromo-2-fluorobenzyl)triphenylphosphonium bromide (3.82 g) and potassium t-butoxide (786 mg) was stirred at room temperature for 30 minutes. Then acetone (1.0 ml) was added and the reaction mixture was heated at reflux for 40 hours. The mixture was filtered, and the filtrate was concentrated. The residue was dissolved in ethyl acetate, washed with water and brine, dried over magnesium sulfate and the solvent was evaporated. The residue was chromatographed on silica gel column eluting with hexane to give 1-(4-bromo-2-fluorophenyl)-2-methyl-1-propene (0.70 g) as an oil.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 40 hours
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed with water and brine
  7. dry with materialdried over magnesium sulfate
  8. customthe solvent was evaporated
  9. customThe residue was chromatographed on silica gel column
  10. washeluting with hexane

Sources & evidence

ORD record
ord-56ddf966df2141d1aa98a3c71090954b
Source dataset
uspto-grants-1994_08
Patent number
US05334716

Reaction notes

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