Potassium Carbonate → 2-Chloro-4-(3-chloro-4-methyl-phenoxy)-benzonitrile

HRID 2386834Notes

Reaction equation

HRID 2386834 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[CH3:8].[Cl:10][C:11]1[CH:18]=[C:17](F)[CH:16]=[CH:15][C:12]=1[C:13]#[N:14].C(=O)([O-])[O-].[K+].[K+]>CN(C)C(=O)C>[Cl:10][C:11]1[CH:18]=[C:17]([O:9][C:4]2[CH:5]=[CH:6][C:7]([CH3:8])=[C:2]([Cl:1])[CH:3]=2)[CH:16]=[CH:15][C:12]=1[C:13]#[N:14]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 148533-Chloro-4-methylphenolHCID 1090002-Chloro-4-fluorobenzonitrile

Product 1

HCID 666970942-Chloro-4-(3-chloro-4-methyl-phenoxy)-benzonitrileYield 99.1%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 3-chloro-4-methylphenol (7.5 g) and 2-chloro-4-fluorobenzonitrile (8.14 g) in N,N-dimethylacetamide (23 ml) was added potassium carbonate (8.55 g). The mixture was stirred for 5 hours at 120° C. The mixture was poured into ice water and extracted with ethyl acetate. The organic phase was washed with water, dried (MgSO4), filtered and concentrated to dryness to give the title compound (14.42 g) as a colorless solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with water
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-923d16048daf4b7d9fefeff90a5c99e1
Source dataset
uspto-grants-2012_09
Patent number
US08268820B2

Reaction notes

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