1,2-Dibromoethane → 1-(3-Chlorophenyl)cyclopropanecarbonitrile

HRID 254810

Reaction equation

HRID 254810 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]#[N:10])[CH:5]=[CH:6][CH:7]=1.Br[CH2:12][CH2:13]Br>C1(C)C=CC=CC=1.[OH-].[Na+].[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2([C:9]#[N:10])[CH2:13][CH2:12]2)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 2

HCID 78391,2-DibromoethaneHCID 73722m-Chlorophenylacetonitrile

Product 1

HCID 151852971-(3-Chlorophenyl)cyclopropanecarbonitrileYield 56.3%

Reagents, catalysts & solvents 4

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 2-(3-chlorophenyl)acetonitrile (3.2 g, 21 mmol) and 1,2-dibromoethane (3 mL, 35 mmol) in toluene (20 ml), 35% sodium hydroxide and tetrabutylammonium iodide (400 mg, 1.3 mmol) were added. The mixture was vigorously stirred at room temperature for 4 hours. The resulting solution was diluted with water and extracted with ethyl acetate. The organic solution was concentrated to afford brown oil. Chromatography on silica gel (hexane/ethyl acetate=5/1) afforded 1-(3-chlorophenyl)cyclopropanecarbonitrile (2.1 g, 56% yield) as light yellow oil.

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationThe organic solution was concentrated
  3. customto afford brown oil

Sources & evidence

ORD record
ord-50a83f5ce8a547809609795fe40542b5
Source dataset
uspto-grants-2011_01
Patent number
US07875647B2

Linked notes

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