1,2-Dibromoethane → HCID 20026167, compound

HRID 1487153Notes

Reaction equation

HRID 1487153 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][C:11]#[N:12])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].Br[CH2:14][CH2:15]Br.[H-].[Na+]>CS(C)=O.CCOCC.CS(C)=O>[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2([C:11]#[N:12])[CH2:15][CH2:14]2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 78391,2-DibromoethaneHCID 121253-NitrophenylacetonitrileHCID 24758Sodium hydride

Product 1

HCID 20026167HCID 20026167, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 19869614Ether dimethylsulfoxideSolvent

Procedure

A solution of 2-(3-nitrophenyl)acetonitrile (2.5 g, 15.42 mmol) and 1,2-dibromoethane (1.329 ml, 15.42 mmol) in DMSO/Et2O (1:1, 10 ml) was added dropwise to a suspension of NaH (1.233 g, 30.8 mmol) in DMSO (Volume: 10 ml, Ratio: 1.000), keeping the temperature at 0° C. Resulting mixture was stirred at ambient temperature for 24 h under N2 atm. The reaction mixture was quenched by addition of IPA (2 ml) and water; partitioned between water (300 ml) and EtOAc (300 ml). The aq. phase was re-extracted with EtOAc (300 ml). Combined organic layers were dried over sodium sulphate and concentrated in vacuo. The residue was purified by flash chromatography to afford 1-(3-nitrophenyl)cyclopropanecarbonitrile (1.799 g, 9.56 mmol).

Workup

  1. customat 0° C
  2. customResulting mixture
  3. customThe reaction mixture was quenched by addition of IPA (2 ml) and water
  4. custompartitioned between water (300 ml) and EtOAc (300 ml)
  5. extractionThe aq. phase was re-extracted with EtOAc (300 ml)
  6. dry with materialCombined organic layers were dried over sodium sulphate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-03398e0d72944a488589dbc9f5d8d7e7
Source dataset
uspto-grants-2016_08
Patent number
US09428499B2

Reaction notes

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