1,2-Dibromoethane → HCID 14798950, compound

HRID 345865Notes

Reaction equation

HRID 345865 reaction equation
[C:1]([CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5])#[N:2].Br[CH2:13][CH2:14]Br.C1OCCOCCOCCOCCOCCOC1.[F-].[K+]>ClCCl>[C:4]([C:3]1([C:1]#[N:2])[CH2:14][CH2:13]1)(=[O:5])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 78391,2-DibromoethaneHCID 2855718-Crown-6HCID 64799BenzoylacetonitrileHCID 522689Potassium Fluoride

Product 1

HCID 14798950HCID 14798950, compoundYield 20.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1 g (7 mmol) of α-cyanoacetophenone, 8 g (43 mmol) of 1,2-dibromoethane, 0.1 g (0.4 mmol) of 18-crown-6 and 4 g (69 mmol) of potassium fluoride are heated under reflux for 18 h as a heterogeneous system in 10 ml of dichloromethane. After cooling, the mixture is filtered, the organic phase is washed with H2O and the solvent is evaporated in vacuo after drying over Na2SO4. The residue is chromatographed on a silica gel using CH2Cl2. 0.25 g (20% of theory) of 1-benzoyl-1-cyanocyclopropane are obtained in this manner as a colorless oil,

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture is filtered
  3. washthe organic phase is washed with H2O
  4. customthe solvent is evaporated in vacuo
  5. dry with materialafter drying over Na2SO4
  6. customThe residue is chromatographed on a silica gel

Sources & evidence

ORD record
ord-d1f5cbc4f007424b8ec05e31f4af6a49
Source dataset
uspto-grants-1991_10
Patent number
US05059615

Reaction notes

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