1,2-Dibromoethane → HCID 89853797, compound

HRID 931158Notes

Reaction equation

HRID 931158 reaction equation
[H-].[Na+].[N:3]1([CH2:8][C:9]#[N:10])[CH:7]=[CH:6][CH:5]=[N:4]1.Br[CH2:12][CH2:13]Br.[Cl-].[NH4+]>CS(C)=O>[N:3]1([C:8]2([C:9]#[N:10])[CH2:13][CH2:12]2)[CH:7]=[CH:6][CH:5]=[N:4]1

Participants

6

Reactant 4

HCID 78391,2-DibromoethaneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 70178431H-pyrazol-1-ylacetonitrile

Product 1

HCID 89853797HCID 89853797, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Sodium hydride (4.65 g, 121 mmol, 60% oil dispersion) was washed with petroleum ether under a nitrogen atmosphere. The supernatant was removed after the suspension settled in order to remove the mineral oil. Then a solution of 2-(1H-pyrazol-1-yl)acetonitrile (3 g, 27 mmol) and 1,2-dibromoethane (6.98 mL, 81 mmol) in dimethylsulfoxide (90 mL) was added at 20° C. over a period of 40 min. The reaction mixture was stirred at room temperature for 5 d. A saturated aqueous solution of ammonium chloride was added and the mixture was stirred at 0° C. for 15 min, extracted with diethyl ether, washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The resulting crude was purified via column chromatography (100-200 mesh silica gel, 5-12% ethyl acetate in petroleum ether) to afford 1-(1H-pyrazol-1-yl)cyclopropanecarbonitrile (1 g, 28%).

Workup

  1. customThe supernatant was removed after the suspension
  2. customto remove the mineral oil
  3. stirringthe mixture was stirred at 0° C. for 15 min
  4. extractionextracted with diethyl ether
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting crude was purified via column chromatography (100-200 mesh silica gel, 5-12% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-27fa49f0335c461f93cc223099020f82
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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