Water → 2-(4-Fluoro-2-methylphenyl)acetonitrile

HRID 1164353Notes

Reaction equation

HRID 1164353 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:4]=1[CH3:10].[C-:11]#[N:12].[K+].O.[I-].[K+]>CC(=O)C>[F:9][C:6]1[CH:7]=[CH:8][C:3]([CH2:2][C:11]#[N:12])=[C:4]([CH3:10])[CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 4875Potassium IodideHCID 9032Potassium CyanideHCID 205118161-(Chloromethyl)-4-fluoro-2-methylbenzene

Product 1

HCID 38654692-(4-Fluoro-2-methylphenyl)acetonitrileYield 87.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 16 parts of 1-(chloromethyl)-4-fluoro-2-methylbenzene, 7.8 parts of a solution of potassium cyanide in a small amount of water, 0.1 parts of potassium iodide and 240 parts of 2-propanone is stirred and refluxed for 22 hours. The reaction mixture is cooled and filtered. The filtrate is evaported. The residue is taken up in water and the product is extracted with methylbenzene. The extract is dried, filtered and evaporated, yielding 13 parts (87.2%) of 4-fluoro-2-methylbenzeneacetonitrile as a residue.

Workup

  1. temperaturerefluxed for 22 hours
  2. temperatureThe reaction mixture is cooled
  3. filtrationfiltered
  4. extractionthe product is extracted with methylbenzene
  5. customThe extract is dried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-a0e0556877194641b9d87def4b3ed5e7
Source dataset
uspto-grants-1983_01
Patent number
US04369184

Reaction notes

Loading…