Ethyl formate → 2-(2,3-Dichlorophenyl)-3-oxo-propionitrile

HRID 1682456Notes

Reaction equation

HRID 1682456 reaction equation
C[CH2:2][O-:3].[Na+].[Cl:5][C:6]1[C:11]([Cl:12])=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:13][C:14]#[N:15].C(OCC)=O>C(O)C>[Cl:5][C:6]1[C:11]([Cl:12])=[CH:10][CH:9]=[CH:8][C:7]=1[CH:13]([CH:2]=[O:3])[C:14]#[N:15]

Participants

5

Reactant 3

HCID 8025Ethyl formate2×HCID 229020Benzeneacetonitrile, 2,3-dichloro-HCID 2723922Sodium ethoxide

Product 1

HCID 197051252-(2,3-Dichlorophenyl)-3-oxo-propionitrileYield 45%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
80 °C

Procedure

To a solution of NaOEt (from 3.63 gms Na) in ethanol (500 ml) was added 2,3-dichlorophenylacetonitrile (Example 14.3) in ethanol (150 ml). Ethyl formate (16.67 gms) was then added and the mixture stirred at 80° C. for 45 minutes, before adding a further quantity of ethyl formate (2.78 gms). After stirring at 80° C. for a further 1.5 hours, the precipitate was filtered off and dried in vacuo. The solid was dissolved in water, filtered, acidified with concentrated hydrochloric acid and the precipitate filtered off and dried in vacuo, 14.35 gms, 45% yield.

Workup

  1. stirringAfter stirring at 80° C. for a further 1.5 hours
  2. filtrationthe precipitate was filtered off
  3. customdried in vacuo
  4. dissolutionThe solid was dissolved in water
  5. filtrationfiltered
  6. filtrationthe precipitate filtered off
  7. customdried in vacuo, 14.35 gms, 45% yield

Sources & evidence

ORD record
ord-bd7d7fb314924c308de592e8dffdcd37
Source dataset
uspto-grants-1997_06
Patent number
US05635507

Reaction notes

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