1,2-Dibromoethane → 1-(4-fluoro-1H-pyrazol-1-yl)cyclopropanecarbonitrile

HRID 931161Notes

Reaction equation

HRID 931161 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:5]=[N:6][N:7]([CH2:9][C:10]#[N:11])[CH:8]=1.Br[CH2:13][CH2:14]Br.[Cl-].[NH4+]>CS(C)=O>[F:3][C:4]1[CH:5]=[N:6][N:7]([C:9]2([C:10]#[N:11])[CH2:14][CH2:13]2)[CH:8]=1

Participants

6

Reactant 4

HCID 78391,2-DibromoethaneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 898539452-(4-Fluoro-1H-pyrazol-1-yl)acetonitrile

Product 1

HCID 898545061-(4-fluoro-1H-pyrazol-1-yl)cyclopropanecarbonitrileYield 22.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Sodium hydride (1.26 g, 52.75 mmol, 60% oil dispersion) was washed with petroleum ether under a nitrogen atmosphere. The supernatant was removed after the solids settled. Then a solution of 2-(4-fluoro-1H-pyrazol-1-yl)acetonitrile (1.1 g, 8.79 mmol) and 1,2-dibromoethane (2.28 mL, 26.37 mmol) in dimethylsulfoxide (90 mL) was added at 0° C. over a period of 40 min. The reaction mixture was stirred at room temperature for 6 h. A saturated aqueous solution of ammonium chloride was added and the mixture was extracted with diethyl ether. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude material was purified via column chromatography (100-200 mesh silica gel, 5-12% ethyl acetate in petroleum ether) to afford 1-(4-fluoro-1H-pyrazol-1-yl)cyclopropanecarbonitrile (300 mg).

Workup

  1. customThe supernatant was removed after the solids
  2. extractionthe mixture was extracted with diethyl ether
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified via column chromatography (100-200 mesh silica gel, 5-12% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-c7645a237faa49b685a978e652400835
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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