1,2-Dibromoethane → 1-(3-Bromophenyl)cyclopropane-1-carbonitrile

HRID 216620

Reaction equation

HRID 216620 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]#[N:10])[CH:5]=[CH:6][CH:7]=1.Br[CH2:12][CH2:13]Br>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.[OH-].[Na+]>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([C:9]#[N:10])[CH2:13][CH2:12]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 78391,2-DibromoethaneHCID 36023(3-Bromophenyl)acetonitrile

Product 1

HCID 200261781-(3-Bromophenyl)cyclopropane-1-carbonitrileYield 95%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 14798Sodium HydroxideSolvent

Procedure

3-Bromophenylacetonitrile (5.0 g, 26 mmol) and 1,2-dibromoethane (6.6 mL, 77 mmol) were added to a solution of benzyltriethylammonium chloride (0.30 g, 1.3 mmol) in 50% sodium hydroxide aqueous solution (20 mL), and the mixture was stirred at room temperature overnight. Ice-water (70 mL) was added to the reaction mixture, and the whole was extracted with ethyl acetate (50 mL). The organic layer was washed with brine (30 mL), and dried over anhydrous magnesium sulfate. After the solvent was evaporated under reduced pressure, the residue was purified by silica gel column chromatography to give the title reference compound (5.4 q) as brown oil (yield 95%).

Workup

  1. extractionthe whole was extracted with ethyl acetate (50 mL)
  2. washThe organic layer was washed with brine (30 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customAfter the solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-15fd5f118daf44cca02e80d71baab603
Source dataset
uspto-grants-2012_06
Patent number
US08193237B2

Linked notes

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