Potassium Cyanide → 4-Phenylbenzoylacetonitrile

HRID 133477Notes

Reaction equation

HRID 133477 reaction equation
[C-:1]#[N:2].[K+].Br[CH2:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:10][CH:9]=1)=[O:7]>O.CC#N>[C:11]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:12]=[CH:13][C:8]([C:6](=[O:7])[CH2:5][C:1]#[N:2])=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 672821-(1,1'-Biphenyl)-4-yl-2-bromoethanone

Product 1

HCID 126868534-PhenylbenzoylacetonitrileYield 118.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 105 mg (1.6 mmol) of KCN in 1 mL of water, 220 mg (0.8 mmol) of 2-bromo-4′-phenylacetophenone in 3 mL of MeCN was added. The mixture was warmed in a 50° C. bath to dissolve some of the halide. After ˜20 min the solids dissolved. The reaction was stirred for 30 min, then partitioned between 1.2 N HCl and EtOAc. The organic layer was washed with brine, dried and concentrated leaving 210 mg of the title compound which was used in the next step without purification.

Workup

  1. dissolutionAfter ˜20 min the solids dissolved
  2. custompartitioned between 1.2 N HCl and EtOAc
  3. washThe organic layer was washed with brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-938f7efe1b624dd0a6560a4a80aeb9bc
Source dataset
uspto-grants-2008_06
Patent number
US07390835B2

Reaction notes

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