Ethyl Acetate → 5-formylthiophene-3-carbonitrile

HRID 1071621Notes

Reaction equation

HRID 1071621 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:7]=[O:8])[S:5][CH:6]=1.[Cu](C#N)[C:10]#[N:11].C(OCC)(=O)C>CN(C=O)C>[C:10]([C:2]1[CH:3]=[C:4]([CH:7]=[O:8])[S:5][CH:6]=1)#[N:11]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 877924-Bromothiophene-2-carbaldehydeHCID 178418260HCID 178418260, compound

Product 1

HCID 122800095-formylthiophene-3-carbonitrileYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Bromo-2-thiophenecarboaldehyde (5.00 g) was dissolved in DMF (40 ml), and copper cyanide (3.52 g) was added thereto. After heating under reflux for 3 hours, the mixture was cooled as it was to room temperature and ethyl acetate was added thereto. The mixture was washed with an aqueous ammonia, water, 0.1N aqueous hydrochloric acid and further brine, dried over anhydrous magnesium sulfate and then evaporated. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate system), and then recrystallized from ethyl acetate-hexane, to give the title compound as pale yellowish white crystals (2.30 g, 71%).

Workup

  1. temperatureAfter heating
  2. temperatureunder reflux for 3 hours
  3. temperaturethe mixture was cooled as it
  4. customwas to room temperature
  5. washThe mixture was washed with an aqueous ammonia, water, 0.1N aqueous hydrochloric acid and further brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated
  8. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate system)
  9. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-dc17af2ea7774310b7d2ec50618d4703
Source dataset
uspto-grants-2005_06
Patent number
US06906072B1

Reaction notes

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