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

HRID 1824936

Reaction equation

HRID 1824936 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-9f1bda2d7be54cefa7131823b99501cf
Source dataset
uspto-grants-2006_05
Patent number
US07045545B1

Linked notes

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