Potassium Carbonate → 3-(2-Nitrophenoxy)benzonitrile

HRID 1609266Notes

Reaction equation

HRID 1609266 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1)#[N:2].F[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N+:17]([O-:19])=[O:18].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[N+:17]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[O:9][C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=1)[C:1]#[N:2])([O-:19])=[O:18]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 133943-CyanophenolHCID 738951-Fluoro-2-nitrobenzene

Product 1

HCID 91948883-(2-Nitrophenoxy)benzonitrileYield 95.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

In 50 ml of N,N-dimethylformamide were dissolved 5.0 g of 3-cyanophenol and 5.93 g of 2-fluoronitrobenzene followed by addition of 8.71 g of potassium carbonate, and the mixture was stirred with heating at 100° C. for 2 hours. After cooling, the reaction mixture was diluted with water and extracted with ethyl acetate. The ethyl acetate layer was washed with water 3 times, dried and concentrated. The residue was crystallized from diisopropyl ether to give 9.63 g of the title compound as light yellow crystals.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water 3 times
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-b9d20eb9d2c6493e9aacf4a758e13cc9
Source dataset
uspto-grants-1995_03
Patent number
US05399703

Reaction notes

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