4-Fluorophenol → Benzene, 1-(3-buten-1-yloxy)-4-fluoro-
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]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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
- temperatureat reflux over 16 hours
- concentrationThe mixture was then concentrated in vacuo
- washwashed with water
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- 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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