Dinitrofluorobenzene → HCID 13252395, compound

HRID 904050Notes

Reaction equation

HRID 904050 reaction equation
C(=O)([O-])[O-].[K+].[K+].[N+:7]([C:10]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:11]=1F)([O-:9])=[O:8].C(=O)(O)[O-].[Na+].[CH3:25][N:26]1[C:30]([OH:31])=[C:29]([C:32](=[O:41])[C:33]2[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][C:34]=2[Cl:40])[C:28]([CH3:42])=[N:27]1>C(C(C)=O)C.C(Cl)Cl>[CH3:25][N:26]1[C:30]([O:31][C:11]2[CH:12]=[CH:13][C:14]([N+:16]([O-:18])=[O:17])=[CH:15][C:10]=2[N+:7]([O-:9])=[O:8])=[C:29]([C:32](=[O:41])[C:33]2[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][C:34]=2[Cl:40])[C:28]([CH3:42])=[N:27]1

Participants

7

Reactant 4

HCID 6264DinitrofluorobenzeneHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 178434070HCID 178434070, compound

Product 1

HCID 13252395HCID 13252395, compoundYield 70.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

In a four necked flask, 1.43 g of 1,3-dimethyl-4-(2,4-dichlorobenzoyl)-5-hydroxypyrazole was dissolved in 15 ml of methyl ethyl ketone and 1.38 g of anhydrous potassium carbonate was added to the solution and 0.93 g of 2,4-dinitrophenylfluoride was added dropwise to the mixture under stirring. After the addition, the reaction was carried out for 3 hours under refluxing. The reaction mixture was filtered and methyl ethyl ketone was distilled off to obtain the precipitate of the reaction product. The precipitate was dissolved in methylene chloride and the solution was mixed with a saturated aqueous solution of sodium bicarbonate. The organic phase was separated and methylene chloride was distilled off to obtain the solid product. The solid product was washed with benzene to obtain 1.58 g of 1,3-dimethyl-4-(2,4-dichlorobenzoyl)-5-(2,4-dinitrophenoxy) pyrazole having a melting point of 190° to 192° C.

Workup

  1. additionwas added dropwise to the mixture
  2. additionAfter the addition
  3. temperatureunder refluxing
  4. filtrationThe reaction mixture was filtered
  5. distillationmethyl ethyl ketone was distilled off
  6. customto obtain the precipitate of the reaction product
  7. customThe organic phase was separated
  8. distillationmethylene chloride was distilled off
  9. customto obtain the solid product
  10. washThe solid product was washed with benzene

Sources & evidence

ORD record
ord-6d7c44b656084ad8b4fad818ec3dd9f9
Source dataset
uspto-grants-1980_10
Patent number
US04230481

Reaction notes

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