1,2-Dibromoethane → 1-(2-Methoxyphenyl)cyclopropane-1-carbonitrile

HRID 440499Notes

Reaction equation

HRID 440499 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]#[N:11].[CH2:12](Br)[CH2:13]Br.[OH-].[K+].C1OCCOCCOCCOCCOCCOC1>CS(C)=O.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1([C:10]#[N:11])[CH2:13][CH2:12]1

Participants

7

Reactant 4

HCID 78391,2-DibromoethaneHCID 14797Potassium HydroxideHCID 2855718-Crown-6HCID 81496(2-Methoxyphenyl)acetonitrile

Product 1

HCID 102196291-(2-Methoxyphenyl)cyclopropane-1-carbonitrile

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Procedure

A mixture of (2-methoxyphenyl)acetonitrile (147 g and 1,2-dibromomethane (168 ml) in dimethylsulphoxide (250 ml) was added over 1 hour to a stirred suspension of powdered potassium hydroxide (250 g) and 18-Crown-6 (5 g) in dimethylsulphoxide (1200 ml) at 25° C. Stirring was continued for 20 hours. Water (1200 ml) was added and the mixture extracted with ether to give a crude oil which was purified by distillation (b.p. 102°/0.25) to give 1-(2-methoxyphenyl)cyclopropane carbonitrile.

Workup

  1. extractionthe mixture extracted with ether
  2. customto give a crude oil which
  3. distillationwas purified by distillation (b.p. 102°/0.25)

Sources & evidence

ORD record
ord-b2648443183f413882b50633aa22920f
Source dataset
uspto-grants-1996_05
Patent number
US05519034

Reaction notes

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