Ethanol → Ethyl 4-chloro-2-fluorophenylacetate

HRID 1870788Notes

Reaction equation

HRID 1870788 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#N)=[C:4]([F:11])[CH:3]=1.[OH2:12].[CH2:13]([OH:15])[CH3:14]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:15][CH2:13][CH3:14])=[O:12])=[C:4]([F:11])[CH:3]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 962WaterHCID 2736569(4-Chloro-2-fluoro-phenyl)-acetonitrile

Product 1

HCID 4518464Ethyl 4-chloro-2-fluorophenylacetate

Procedure

Then, 15.1 g of 4-chloro-2-fluorophenylacetonitrile was dissolved in 150 ml of ethanol, to which 10 ml of suiliric acid was added, and the mixture was heated under reflux for 65 hours. After completion of the reaction, the reaction mixture was 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 17.8 g of ethyl 4-chloro-2-fluorophenylacetate.

Workup

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 65 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-ec371970c6ee4d6484cf44691cd0ef7b
Source dataset
uspto-grants-2000_08
Patent number
US06100257

Reaction notes

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