Potassium Cyanide → 2-[4-(Difluoromethoxy)phenyl]acetonitrile

HRID 1995674Notes

Reaction equation

HRID 1995674 reaction equation
[C-:1]#[N:2].[K+].[F:4][CH:5]([F:15])[O:6][C:7]1[CH:14]=[CH:13][C:10]([CH2:11]Br)=[CH:9][CH:8]=1>O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[F:4][CH:5]([F:15])[O:6][C:7]1[CH:14]=[CH:13][C:10]([CH2:11][C:1]#[N:2])=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 27370014-(Difluoromethoxy)benzyl Bromide

Product 1

HCID 27370182-[4-(Difluoromethoxy)phenyl]acetonitrileYield 81.6%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

100 g of potassium cyanide were dissolved in 160 ml of water, and 15 g of tetrabutylammonium bromide and 230 g of 4-difluoromethoxy-benzyl bromide were then added. The mixture was then heated to 100° C. for 1 hour and, after cooling, was extracted twice with methylene chloride. After drying over sodium sulphate, the organic phase was first freed from solvent and then distilled. 145 g of 4-difluoromethoxy-benzyl cyanide were obtained. Boiling point=106°-8° C./0.3 mm Hg; nD20 =1.4822.

Workup

  1. temperatureafter cooling
  2. extractionwas extracted twice with methylene chloride
  3. dry with materialAfter drying over sodium sulphate
  4. distillationdistilled

Sources & evidence

ORD record
ord-c0376e7060174239b01caac53e0e72b1
Source dataset
uspto-grants-1983_09
Patent number
US04405639

Reaction notes

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