Ethanol → (4-Chloro-2-fluoro-phenyl)-acetonitrile

HRID 1870787Notes

Reaction equation

HRID 1870787 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Cl)=[C:4]([F:10])[CH:3]=1.C(O)C.[C-:14]#[N:15].[Na+]>O>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][C:14]#[N:15])=[C:4]([F:10])[CH:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 8929Sodium CyanideHCID 148779334-Chloro-1-(chloromethyl)-2-fluorobenzene

Product 1

HCID 2736569(4-Chloro-2-fluoro-phenyl)-acetonitrileYield 86.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Then, 18.5 g of 4-chloro-2-fluorobenzyl chloride was dissolved in a mixed solvent consisting of 130 ml of ethanol and 30 ml of water, to which 5.3 g of sodium cyanide was added, and the mixture was heated under reflux for 2 hours. After completion of the reaction, the reaction mixture was allowed to stand for cooling to room temperature, poured into water, and extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried, and concentrated. The residue was subjected to silica gel column chromatography, which afforded 15.1 g of 4-chloro-2-fluorophenylacetonitrile.

Workup

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 2 hours
  4. customAfter completion of the reaction
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with saturated sodium chloride solution
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-e3b9ea215b1d4374a45eff06456e2319
Source dataset
uspto-grants-2000_08
Patent number
US06100257

Reaction notes

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