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

HRID 1106720Notes

Reaction equation

HRID 1106720 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 9) 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-745dd163921f42ab8dec33e6b2ebe2f4
Source dataset
uspto-grants-2000_05
Patent number
US06057349

Reaction notes

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