Water → 2-Fluoro-4-methoxybenzonitrile
Reaction equation
[F:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[C:11](=O)([O-])[O-].[K+].[K+].IC.O>CN(C=O)C>[F:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
2-Fluoro-4-hydroxybenzonitrile (0.50 g, 3.7 mmol), potassium carbonate (0.53 g, 3.8 mmol) and iodomethane (0.34 mL, 0.78 g, 5.5 mmol) in dry DMF (5 mL) were stirred at ambient temperature for 21 h. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with 1N sodium hydroxide solution (2×), water (3×), brine (1×), and dried over MgSO4. After filtration, the solvent was removed in vacuo to yield 2-fluoro-4-methoxy-benzonitrile (0.54 g, 98%) as a white crystalline solid.
Workup
- extractionextracted with ethyl acetate
- washThe ethyl acetate layer was washed with 1N sodium hydroxide solution (2×), water (3×), brine (1×)
- dry with materialdried over MgSO4
- filtrationAfter filtration
- customthe solvent was removed in vacuo
Sources & evidence
- ORD record
- ord-d99df65aa78b4675b0b8cf9cda64d46f
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07119122B2
Reaction notes
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