1,4-Dibromobutane → 1-(2-Chlorophenyl)cyclopentane-1-carbonitrile

HRID 440537Notes

Reaction equation

HRID 440537 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]#[N:10].Br[CH2:12][CH2:13][CH2:14][CH2:15]Br.[OH-].[K+]>CS(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([C:9]#[N:10])[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 80561,4-DibromobutaneHCID 14797Potassium HydroxideHCID 76112(o-Chlorophenyl)acetonitrile

Product 1

HCID 157427181-(2-Chlorophenyl)cyclopentane-1-carbonitrileYield 61.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A mixture of 2-chlorophenylacetonitrile (20 g), 1,4-dibromobutane (28.5 g) and dimethyl sulphoxide (100 ml) was added dropwise to a stirred suspension of powdered potassium hydroxide (26 g) in dry dimethylsulphoxide (300 ml). The mixture was stirred for one hour, then poured onto ice/water and extracted with ethyl acetate. The extracts yielded an oil which was distilled under vacuum (b.p. 112°-116° C./1 mbar) to give 1-(2-chlorophenyl)cyclopentanecarbonitrile (16.7 g).

Workup

  1. additionpoured onto ice/water
  2. extractionextracted with ethyl acetate
  3. customThe extracts yielded an oil which
  4. distillationwas distilled under vacuum (b.p. 112°-116° C./1 mbar)

Sources & evidence

ORD record
ord-d4d6b0ed3d174df69eb4aa5a99174889
Source dataset
uspto-grants-1996_05
Patent number
US05519034

Reaction notes

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