Dinitrofluorobenzene → HCID 14324511, compound

HRID 1588387Notes

Reaction equation

HRID 1588387 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1F)([O-:3])=[O:2].[C:14]([C:18]1[O:22][N:21]=[C:20]([OH:23])[CH:19]=1)([CH3:17])([CH3:16])[CH3:15].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:14]([C:18]1[O:22][N:21]([C:5]2[CH:6]=[CH:7][C:8]([N+:10]([O-:12])=[O:11])=[CH:9][C:4]=2[N+:1]([O-:3])=[O:2])[C:20](=[O:23])[CH:19]=1)([CH3:17])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 6264DinitrofluorobenzeneHCID 11430Potassium CarbonateHCID 178441207HCID 178441207, compound

Product 1

HCID 14324511HCID 14324511, compoundYield 31.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

After mixing 3.7 g of 2,4-dinitrofluorobenzene, 20 ml of dimethylformamide, 2.9 g of 5-t-butyl-3-hydroxyisoxazole, and 2.8 g of potassium carbonate, the reaction was performed for 30 minutes at 80° C. and after cooling the reaction mixture, the product formed was extracted with a mixture of diethyl ether and ethyl acetate. The solvent was distilled off from the extract under reduced pressure and the residue obtained was crystallized from a mixture of diethyl ether and ethyl acetate to provide 1.9 g of the desired compound with a yield of 30.9%. The melting point thereof was 167° C. to 168° C.

Workup

  1. temperatureafter cooling the reaction mixture
  2. customthe product formed
  3. extractionwas extracted with a mixture of diethyl ether and ethyl acetate
  4. distillationThe solvent was distilled off from the
  5. extractionextract under reduced pressure
  6. customthe residue obtained
  7. customwas crystallized from a mixture of diethyl ether and ethyl acetate

Sources & evidence

ORD record
ord-17659463e04a47e186be0b6c10b4af21
Source dataset
uspto-grants-1993_06
Patent number
US05221750

Reaction notes

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