Water → 4-Fluoro-5-formyl-2-methoxybenzonitrile

HRID 503204Notes

Reaction equation

HRID 503204 reaction equation
Br[C:2]1[C:3]([O:11][CH3:12])=[CH:4][C:5]([F:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].[Cu](C#N)[C:14]#[N:15].O>CN1CCCC1=O>[F:10][C:5]1[C:6]([CH:7]=[O:8])=[CH:9][C:2]([C:14]#[N:15])=[C:3]([O:11][CH3:12])[CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 121872105-Bromo-2-fluoro-4-methoxybenzaldehydeHCID 178418260HCID 178418260, compound

Product 1

HCID 222609964-Fluoro-5-formyl-2-methoxybenzonitrileYield 25.8%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
180 °C

Procedure

5.33 g of 5-bromo-2-fluoro-4-methoxy-benzaldehyde was dissolved in 73 ml of 1-methyl-2-pyrrolidone, 2.46 g of copper cyanide was added under stirring at 180° C. for 5.5 hours. After cooling to room temperature, water was added to the reaction mixture. The mixture was extracted with ethyl acetate and filtered through Celite. Then, the resulting organic layer was washed with water and brine, dried over magnesium sulfate and the solvent was evaporated. The residue was purified and separated by silica gel column chromatography, to give 0.983 g of the title compound as pale yellow crystals.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionThe mixture was extracted with ethyl acetate
  3. filtrationfiltered through Celite
  4. washThen, the resulting organic layer was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent was evaporated
  7. customThe residue was purified
  8. customseparated by silica gel column chromatography

Sources & evidence

ORD record
ord-0da8ae68546a42949f55c64fddcef40e
Source dataset
uspto-grants-2010_08
Patent number
US07776890B2

Reaction notes

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