4-Fluorophenol → Benzene, 1-(3-buten-1-yloxy)-4-fluoro-

HRID 2395419Notes

Reaction equation

HRID 2395419 reaction equation
Br[CH2:2][CH2:3][CH:4]=[CH2:5].[F:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[F:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:5][CH2:4][CH:3]=[CH2:2])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 97324-FluorophenolHCID 11430Potassium CarbonateHCID 21241Homoallyl bromide

Product 1

HCID 18971814Benzene, 1-(3-buten-1-yloxy)-4-fluoro-Yield 36%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 4-bromo-1-butene (4.0 g), 4-fluorophenol (3.0 g), potassium carbonate (3.8 g) and acetone (75 ml) was heated at reflux over 16 hours. The mixture was then concentrated in vacuo, dluted with ether, washed with water followed by 1N sodium hydroxide, dried over sodium sulfate, filtered, and concentrated in vacuo. Chromatography on a silica gel column eluting with 25% ethyl acetate-hexane afforded 1.6 g of a colorless oil.

Workup

  1. temperatureat reflux over 16 hours
  2. concentrationThe mixture was then concentrated in vacuo
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. washChromatography on a silica gel column eluting with 25% ethyl acetate-hexane

Sources & evidence

ORD record
ord-8da0142d35ed43beaa759a5b59177616
Source dataset
uspto-grants-1998_09
Patent number
US05814651

Reaction notes

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