1,2-Dibromoethane → 1-(3,5-Difluorophenyl)cyclopropanecarbonitrile

HRID 1026155Notes

Reaction equation

HRID 1026155 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]#[N:11])[CH:5]=[C:6]([F:8])[CH:7]=1.Br[CH2:13][CH2:14]Br.[OH-].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O>[F:1][C:2]1[CH:3]=[C:4]([C:9]2([C:10]#[N:11])[CH2:14][CH2:13]2)[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

6

Reactant 3

HCID 78391,2-DibromoethaneHCID 14798Sodium HydroxideHCID 5185653,5-Difluorophenylacetonitrile

Product 1

HCID 534026771-(3,5-Difluorophenyl)cyclopropanecarbonitrile

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

To a mixture of 3,5-difluoro-phenylacetonitrile (11.48 g), 1,2-dibromoethane (42.2 ml) and benzyltriethylammonium chloride (0.68 g) was added sodium hydroxide solution (50% in water, 30 ml) at room temperature. The mixture was vigorously stirred overnight. Water was added and the aqueous phase was extracted twice with diethyl ether. The combined organic layers were washed with water and brine, dried over MgSO4 and concentrated. The residue was purified by column chromatography (SiO2; heptane/EtOAc) to give 1-(3,5-difluoro-phenyl)cyclopropanecarbonitrile as a light pink solid (8.23 g). 1H-NMR (300 MHz, CDCl3, δ): 1.40-1.44, (m, 2H), 1.78-1.82 (m, 2H), 6.70-6.85 (m, 3H).

Workup

  1. extractionthe aqueous phase was extracted twice with diethyl ether
  2. washThe combined organic layers were washed with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (SiO2; heptane/EtOAc)

Sources & evidence

ORD record
ord-5e08efd61c3240be8d483a62b3bab7c6
Source dataset
uspto-grants-2014_05
Patent number
US08729113B2

Reaction notes

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