HCID 22227870, compound → 3'-Cyano-4'-isobutylacetophenone

HRID 1744517Notes

Reaction equation

HRID 1744517 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:12](=[O:14])[CH3:13])[CH:5]=[CH:6][C:7]=1[CH2:8][CH:9]([CH3:11])[CH3:10].[Cu](C#N)[C:16]#[N:17]>CN(C)C=O>[C:16]([C:2]1[CH:3]=[C:4]([C:12](=[O:14])[CH3:13])[CH:5]=[CH:6][C:7]=1[CH2:8][CH:9]([CH3:11])[CH3:10])#[N:17]

Participants

4

Reactant 2

HCID 22227870HCID 22227870, compoundHCID 178418260HCID 178418260, compound

Product 1

HCID 222280063'-Cyano-4'-isobutylacetophenoneYield 48.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3′-Bromo-4′-isobutylacetophenone (182 g) and copper cyanide (95.7 g) were stirred in dimethylformamide (520 ml) at 140° C. for 7 h. The reaction mixture was cooled to room temperature and the solid was filtered off. To the filtrate was added water and the mixture was extracted with toluene. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, after which the solvent was evaporated under reduced pressure. The residue was recrystallized from n-hexane to give 3′-cyano-4′-isobutylacetophenone (70 g), melting point: 71–72° C.

Workup

  1. filtrationthe solid was filtered off
  2. additionTo the filtrate was added water
  3. extractionthe mixture was extracted with toluene
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customafter which the solvent was evaporated under reduced pressure
  7. customThe residue was recrystallized from n-hexane

Sources & evidence

ORD record
ord-3f4a7661515c43a2b1f9a95098ccb2c5
Source dataset
uspto-grants-2006_03
Patent number
US07015218B1

Reaction notes

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