Isopropanol → 1-(4-Chlorophenyl)cyclobutanecarbonitrile

HRID 325867Notes

Reaction equation

HRID 325867 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][C:7]#[N:8])=[CH:4][CH:3]=1.Br[CH2:12][CH2:13][CH2:14]Br.[H-].[Na+].CC(O)C>CS(C)=O.O>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]2([C:7]#[N:8])[CH2:14][CH2:13][CH2:12]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 3776IsopropanolHCID 80011,3-DibromopropaneHCID 24758Sodium hydrideHCID 2415824-Chlorobenzyl cyanide

Product 1

HCID 986211-(4-Chlorophenyl)cyclobutanecarbonitrile

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Procedure

A solution of 4-chlorobenzyl cyanide (10 g) and 1,3-dibromopropane (7.5 ml) in dry dimethyl sulphoxide (12 ml) was added dropwise under nitrogen to a stirred mixture of sodium hydride (3.6 g) dispersed in mineral oil (3,6 g) and dimethylsulphoxide (70 ml) at a temperature in the range 30° to 35° C. The mixture was stirred at room temperature for two hours and then propan-2-ol (10 ml) and water (150 ml) were added dropwise. The mixture was filtered through a diatomaceous earth sold under the Registered Trade Mark CELITE and the solid residue washed with ether. The filtrate was extracted with ether and the ether phases combined, washed with water, dried and evaporated. 1-(4-chlorophenyl)-1-cyclobutanecarbonitrile (b.p. 116°-120° at 0.6 mm Hg) was isolated by distillation. This method is a modification of that described by Butler and Pollatz (J.Org.Chem., Vol. 36, No. 9, 1971, p. 1308).

Workup

  1. filtrationThe mixture was filtered through a diatomaceous earth
  2. washthe solid residue washed with ether
  3. extractionThe filtrate was extracted with ether
  4. washwashed with water
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-7b12849283d9469f83ce62d73269ede3
Source dataset
uspto-grants-1984_04
Patent number
US04443449

Reaction notes

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