Isopropanol → 1-(3,4-Dichlorophenyl)-1-cyclobutane-carbonitrile

HRID 365634Notes

Reaction equation

HRID 365634 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[CH2:5][C:6]#[N:7].Br[CH2:13][CH2:14][CH2:15]Br.[H-].[Na+].CC(O)C>CS(C)=O.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2([C:6]#[N:7])[CH2:15][CH2:14][CH2:13]2)[CH:8]=[CH:9][C:10]=1[Cl:11]

Participants

7

Reactant 4

HCID 3776IsopropanolHCID 80011,3-DibromopropaneHCID 24758Sodium hydrideHCID 76690(3,4-Dichlorophenyl)acetonitrile

Product 1

HCID 108571341-(3,4-Dichlorophenyl)-1-cyclobutane-carbonitrile

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Procedure

A solution of 3,4-dichlorobenzyl cyanide (25 g) and 1,3-dibromopropane (15 ml) in dry dimethyl sulfoxide (150 ml) was added dropwise under nitrogen to a stirred mixture of sodium hydride (7.5 g), which was dispersed in mineral oil (7.5 g), and dimethyl sulfoxide (200 ml) at 30-35° C. The mixture was stirred at room temperature for 2 hours, and 2-propanol (8 ml) and then water (110 ml) were added dropwise. The mixture was filtered through diatomaceous earth which is marketed under the proprietary name CELITE, and the solid residue was washed with ether. The ether layer was separated off, washed with water, dried and evaporated. 1-(3,4-dichlorophenyl)-1-cyclobutane-carbonitrile was isolated by distillation (boiling point: 108 to 120° C. under 0.2 mbar. This procedure is a modification of the process described by Butler and Pllatz (J. Org. Chem. 36 No. 9 (1971) 1308).

Workup

  1. filtrationThe mixture was filtered through diatomaceous earth which
  2. washthe solid residue was washed with ether
  3. customThe ether layer was separated off
  4. washwashed with water
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-8a0940e741a1475d8c37b606d8829a18
Source dataset
uspto-grants-2000_10
Patent number
US06127424

Reaction notes

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