Allyl bromide → 3-Bromo-4-fluorophenyl allyl ether

HRID 1815812Notes

Reaction equation

HRID 1815812 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[F:8].[CH2:10](Br)[CH:11]=[CH2:12].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:12]([O:9][C:4]1[CH:5]=[CH:6][C:7]([F:8])=[C:2]([Br:1])[CH:3]=1)[CH:11]=[CH2:10]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 27833813-Bromo-4-Fluorophenol

Product 1

HCID 221447733-Bromo-4-fluorophenyl allyl etherYield 61%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 0.65 gm (3.43 mMol) 3-bromo-4-fluorophenol, 0.60 mL (6.86 mMol) allyl bromide, and 0.71 gm (5.15 mMol) potassium carbonate in 6 mL acetone was stirred at reflux for 13 hours. The reaction mixture was concentrated under reduced pressure and the residue subjected to silica gel chromatography, eluting with hexane. Fractions containing product were combined and concentrated under reduced pressure to provide 61% of the desired compound.

Workup

  1. temperatureat reflux for 13 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. washeluting with hexane
  4. additionFractions containing product
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5ee9e77b515b49c19f3f69c2293207d2
Source dataset
uspto-grants-2005_04
Patent number
US06881733B1

Reaction notes

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