Ethyl Acetate → 3-(Cyanomethyl)benzonitrile

HRID 1717105Notes

Reaction equation

HRID 1717105 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7].[C-:11]#[N:12].[K+].CCOC(C)=O>CN(C=O)C.O>[C:11]([CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7])#[N:12]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 9032Potassium CyanideHCID 97249Benzonitrile, 3-(bromomethyl)-

Product 1

HCID 5192803-(Cyanomethyl)benzonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

3-Bromomethyl-benzonitrile (150 mg, 0.76 mmol) was dissolved in DMF (2 ml). KCN (55 mg, 0.84 mmol) was dissolved in the minimum amount of water and was added to the reaction. The resulting solution was stirred at 85° C. overnight. The reaction mixture was allowed to cool to room temperature, EtOAc (5 ml) was added, and the solution was washed with saturated NaHCO3 (4×10 ml). The organic layer was dried (MgSO4), filtered and the solvent removed in vacuo to give the title compound.

Workup

  1. additionwas added to the reaction
  2. temperatureto cool to room temperature
  3. washthe solution was washed with saturated NaHCO3 (4×10 ml)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-733406cc73a6499fa139f890f6ca8bfc
Source dataset
uspto-grants-2010_09
Patent number
US07803841B2

Reaction notes

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