1,2-Dibromoethane → 1-(4-Bromophenyl)Cyclopropanecarbonitrile

HRID 919049Notes

Reaction equation

HRID 919049 reaction equation
[OH-].[K+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]#[N:12])=[CH:6][CH:5]=1.Br[CH2:14][CH2:15]Br>O.C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:11]#[N:12])[CH2:15][CH2:14]2)=[CH:6][CH:5]=1

Participants

7

Reactant 3

HCID 78391,2-DibromoethaneHCID 14797Potassium HydroxideHCID 27914Benzeneacetonitrile, 4-bromo-

Product 1

HCID 27952731-(4-Bromophenyl)Cyclopropanecarbonitrile

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Potassium hydroxide (14.3 g, 255 mmol) was dissolved in H2O (5 mL) and toluene (40 mL). 4-Bromophenylacetonitrile (5.0 g, 25.5 mmol) and tetrabutylammonium bromide (0.41 g, 1.3 mmol) were added, and 1,2-dibromoethane (3.25 mL, 38 mmol) was added dropwise over 10 minutes. The reaction was stirred at room temperature for 2 hours and then submitted to standard aqueous workup and concentrated to give the title compound.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-c07146418f25428692279a310946d585
Source dataset
uspto-grants-2016_03
Patent number
US09272990B2

Reaction notes

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