Dinitrofluorobenzene → HCID 22646056, compound

HRID 393495Notes

Reaction equation

HRID 393495 reaction equation
[OH:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:15])=[O:7])=[CH:4][CH:3]=1.[N+:18]([C:21]1[CH:26]=[C:25]([N+:27]([O-:29])=[O:28])[CH:24]=[CH:23][C:22]=1F)([O-:20])=[O:19].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[N+:18]([C:21]1[CH:26]=[C:25]([N+:27]([O-:29])=[O:28])[CH:24]=[CH:23][C:22]=1[O:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:15])=[O:7])=[CH:4][CH:3]=1)([O-:20])=[O:19]

Participants

5

Reactant 3

HCID 6264DinitrofluorobenzeneHCID 11430Potassium CarbonateHCID 725062SBB015760

Product 1

HCID 22646056HCID 22646056, compoundYield 90.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

0.990 g (4.356 mmol) of 4-hydroxy-2′-methylbenzanilide and 0.811 g (4.358 mmol) of 2,4-dinitrofluorobenzene were dissolved into 20 ml of acetone. The solution was stirred for one hour at reflux temperature after the addition of 0.6 g (4.3 mmol) of potassium carbonate. The reaction solution was filtered and precipitate was thoroughly washed with acetone. Filtrate was concentrated and purified through column chromatography (developing solvent: chloroform) to yield 1.553 g of 4-(2,4-dinitrophenoxy)-2′-methybenzanilide shown in the structural formula 11 above in light yellow solid (Yield: 90.63%).

Workup

  1. temperatureat reflux temperature
  2. filtrationThe reaction solution was filtered
  3. washprecipitate was thoroughly washed with acetone
  4. concentrationFiltrate was concentrated
  5. custompurified through column chromatography (developing solvent: chloroform)

Sources & evidence

ORD record
ord-8db733be8cda4f35b9fc103c7f69aada
Source dataset
uspto-grants-2004_10
Patent number
US06808766B1

Reaction notes

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