1-Bromo-2-Chloroethane → 1-(4-Vinylphenyl)cyclopropanecarbonitrile

HRID 2275615Notes

Reaction equation

HRID 2275615 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]#[N:11])=[CH:5][CH:4]=1)=[CH2:2].Br[CH2:13][CH2:14]Cl>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.[OH-].[Na+].O>[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2([C:10]#[N:11])[CH2:14][CH2:13]2)=[CH:5][CH:4]=1)=[CH2:2]

Participants

6

Reactant 2

HCID 78491-Bromo-2-ChloroethaneHCID 3944539(4-Vinylphenyl)acetonitrile

Product 1

HCID 666626411-(4-Vinylphenyl)cyclopropanecarbonitrile

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of (4-vinylphenyl)acetonitrile (2.1 g, 0.015 mol), 1-bromo-2-chloro-ethane (1.4 mL, 0.016 mol) and benzyltriethylammonium chloride (0.2 g, 0.0008 mol) in aqueous sodium hydroxide solution (20 m, 6 mL) was stirred at 70° C. for 1 h. The reaction mixture was cooled, diluted with water and extracted with ethyl ether. The combined ether layers were washed with water and brine, dried and concentrated to afford the product.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl ether
  3. washThe combined ether layers were washed with water and brine
  4. customdried
  5. concentrationconcentrated
  6. customto afford the product

Sources & evidence

ORD record
ord-cc86b2e274fe4ec18b0babbd991396dc
Source dataset
uspto-grants-2015_09
Patent number
US09126927B2

Reaction notes

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