1,2-Dibromoethane → HCID 67179206, compound

HRID 885192Notes

Reaction equation

HRID 885192 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]#[N:11])[CH:5]=[CH:6][C:7]=1[F:8].Br[CH2:13][CH2:14]Br.[OH-].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:10]#[N:11])[CH2:14][CH2:13]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

6

Reactant 3

HCID 78391,2-DibromoethaneHCID 14798Sodium HydroxideHCID 27737253-Chloro-4-fluorobenzyl cyanide

Product 1

HCID 67179206HCID 67179206, compound

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

To a mixture of 3-chloro-4-fluoro-phenylacetonitrile (8.48 g), 1,2-dibromoethane (13 ml) and benzyltriethylammonium chloride (0.46 g) was added sodium hydroxide solution (50% in water, 20 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-chloro-4-fluorophenyl)-cyclopropanecarbonitrile as light yellow liquid (3.91 g). 1H-NMR (300 MHz, CDCl3, δ): 1.35-1.40 (m, 2H), 1.72-1.76 (m, 2H), 7.10-7.21 (m, 2H), 7.26-7.34 (m, 1H).

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-bec544da61e94040a6c431c140c10b10
Source dataset
uspto-grants-2012_08
Patent number
US08242153B2

Reaction notes

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