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

HRID 504363

Reaction equation

HRID 504363 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-e07ed7f6a19d48b0b639df4a461bf8be
Source dataset
uspto-grants-2010_08
Patent number
US07776874B2

Linked notes

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