Water → 2,5-Difluorophenol allyl ether
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[OH:9].C(=O)([O-])[O-].[K+].[K+].[CH2:16](Br)[CH:17]=[CH2:18].O>CC(C)=O>[CH2:18]([O:9][C:3]1[CH:4]=[C:5]([F:8])[CH:6]=[CH:7][C:2]=1[F:1])[CH:17]=[CH2:16]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
2,5-Difluorophenol (10 g) was dissolved in dimethylformaldehyde (120 ml). At room temperature, potassium carbonate (21 g) and allyl bromide (8.57 ml) were successively added to the mixture and it was stirred at 80° C. for 1 hr. After adding water to the liquid reaction mixture, it was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solvent: 5% ethyl acetate/n-hexane) to give 2,5-difluorophenol allyl ether (13 g) as a colorless oil.
Workup
- customto the liquid reaction mixture, it
- extractionwas extracted with ethyl acetate
- washThe organic layer was washed with brine
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe resulting residue was purified by silica gel column chromatography (developing solvent: 5% ethyl acetate/n-hexane)
Sources & evidence
- ORD record
- ord-b9eff78da3134a83b0fd18fb16fc19af
- Source dataset
- uspto-grants-2001_07
- Patent number
- US06258811B1
Reaction notes
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