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

HRID 557900

Reaction equation

HRID 557900 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 (20m, 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-6f89eb4704a341899b0d4caa84791139
Source dataset
uspto-grants-2011_11
Patent number
US08058288B2

Linked notes

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