Potassium Carbonate → (4-Chloro-2-methyl-3-nitrophenoxy)acetonitrile

HRID 618215Notes

Reaction equation

HRID 618215 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH3:9])[C:3]=1[N+:10]([O-:12])=[O:11].Br[CH2:14][C:15]#[N:16].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:14][C:15]#[N:16])=[C:4]([CH3:9])[C:3]=1[N+:10]([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 187896364-Chloro-2-methyl-3-nitrophenol

Product 1

HCID 18789663(4-Chloro-2-methyl-3-nitrophenoxy)acetonitrile

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-chloro-2-methyl-3-nitrophenol (7.6 g), bromoacetonitrile (3.4 mL), and potassium carbonate (16.8 g) in 2-butanone (80 mL) was heated at 80° C. for 2 hr under an atmosphere of nitrogen. The reaction mixture was cooled to room temperature, then filtered to remove the salts. The filtrate was diluted with ethyl ether (200 mL), washed with saturated sodium chloride solution, and dried over magnesium sulfate. Evaporation of the solvent afforded a yellow solid (9.1 g).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. customto remove the salts
  4. additionThe filtrate was diluted with ethyl ether (200 mL)
  5. washwashed with saturated sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-ce9f9009324647548b5d209bc97c9679
Source dataset
uspto-grants-1999_09
Patent number
US05952362

Reaction notes

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