Water → 2-Fluoro-4-methoxybenzonitrile

HRID 1243719Notes

Reaction equation

HRID 1243719 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

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 27346752-Fluoro-4-hydroxybenzonitrile

Product 1

HCID 6398782-Fluoro-4-methoxybenzonitrileYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with 1N sodium hydroxide solution (2×), water (3×), brine (1×)
  3. dry with materialdried over MgSO4
  4. filtrationAfter filtration
  5. 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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