Dimethyl Sulfoxide → HCID 54075573, compound

HRID 440536Notes

Reaction equation

HRID 440536 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]#[N:10].I[CH2:12][C:13]([CH3:17])(C)[CH2:14]I.[OH-].[K+].[CH3:20]S(C)=O>>[CH3:12][C:13]1([CH3:17])[CH2:14][CH2:20][C:8]1([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1])[C:9]#[N:10]

Participants

5

Reactant 4

HCID 679Dimethyl Sulfoxide2×HCID 14797Potassium HydroxideHCID 76112(o-Chlorophenyl)acetonitrileHCID 3134881,3-diiodo-2,2-dimethylpropane

Product 1

HCID 54075573HCID 54075573, compound

Procedure

A mixture of 2-chlorophenylacetonitrile (26.5 g), 1,3-diiodo-2,2-dimethylpropane (56 g) and dimethyl sulphoxide (300 ml) was added dropwise to a stirred suspension of powdered potassium hydroxide (40 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 to give 2,2-dimethyl-1-(2-chlorophenyl)cyclobutane carbonitrile, (b.p. 116°-120° C./1 mbar) which was recrystallised from petroleum ether (b.p. 60°-80° C.) m.p. 65°-69° C.

Workup

  1. additionpoured onto ice/water
  2. extractionextracted with ethyl acetate
  3. customThe extracts yielded an oil which
  4. distillationwas distilled under vacuum

Sources & evidence

ORD record
ord-0c5f62edcd334221bfb3e10522be37aa
Source dataset
uspto-grants-1996_05
Patent number
US05519034

Reaction notes

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