1,2-Dibromoethane → 1-(3-Trifluoromethyl-phenyl)-cyclopropanecarbonitrile

HRID 1722913Notes

Reaction equation

HRID 1722913 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([CH2:9][C:10]#[N:11])[CH:6]=[CH:7][CH:8]=1.Br[CH2:15][CH2:16]Br.[OH-].[Na+]>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.O>[F:1][C:2]([F:12])([F:13])[C:3]1[CH:4]=[C:5]([C:9]2([C:10]#[N:11])[CH2:16][CH2:15]2)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 78391,2-DibromoethaneHCID 14798Sodium HydroxideHCID 75360m-Trifluoromethylphenylacetonitrile

Product 1

HCID 200261771-(3-Trifluoromethyl-phenyl)-cyclopropanecarbonitrileYield 79.1%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

To a mixture of 3-(trifluoromethyl)phenylacetonitrile (18.5 g, 0.1 mole), 1,2-dibromoethane (56.4 g, 0.3 mole) and triethylbenzylammonium chloride (TEBA) (1.0 g), there was added 40 ml of 50% sodium hydroxide solution at room temperature. The exothermic reaction mixture was vigorously stirred overnight. The reaction mixture was diluted with water (100 ml) and extracted with ether (4×100 ml). The organic layer was washed with water (3×50 ml), brine (50 ml) and dried over magnesium sulfate. The solvent was removed and the product was distilled under reduced pressure (B.P. 92°-94° C. at 0.4 mm Hg) to give a 16.7 g of product (79% yield). ##STR4## where Xn is 4-chloro; 2-bromo; 3-bromo; 2-iodo; 3-iodo; 4-iodo; 3-carboxylic acid; 3-NO3 ; 2,3-benzo.

Workup

  1. extractionextracted with ether (4×100 ml)
  2. washThe organic layer was washed with water (3×50 ml), brine (50 ml)
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was removed
  5. distillationthe product was distilled under reduced pressure (B.P. 92°-94° C. at 0.4 mm Hg)

Sources & evidence

ORD record
ord-727a3c1c59834381921bd7018a1d2348
Source dataset
uspto-grants-1989_08
Patent number
US04859232

Reaction notes

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