Dinitrofluorobenzene → HCID 15637191, compound

HRID 1587481Notes

Reaction equation

HRID 1587481 reaction equation
Cl.[Cl:2][CH2:3][C:4]1[N:5]=[CH:6][NH:7][CH:8]=1.[N+:9]([C:12]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:13]=1F)([O-:11])=[O:10].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[N+:9]([C:12]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:13]=1[N:7]1[CH:8]=[C:4]([CH2:3][Cl:2])[N:5]=[CH:6]1)([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 6264DinitrofluorobenzeneHCID 11430Potassium CarbonateHCID 178478565HCID 178478565, compound

Product 1

HCID 15637191HCID 15637191, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-(Chloromethyl)imidazole hydrochloride (790 mg) was dissolved in 20 ml of acetonitrile. To this solution was added 713 μL of 2,4-dinitrofluorobenzene and 2.14 g of potassium carbonate. The reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure and the residue was partitioned between ethyl acetate and water. The organic layer was dried (sodium sulfate) and concentrated. The crude reaction product was purified by flash silica gel chromatography (8:2 ethyl acetate-hexane elution) to give 745 mg of the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was partitioned between ethyl acetate and water
  3. dry with materialThe organic layer was dried (sodium sulfate)
  4. concentrationconcentrated
  5. customThe crude reaction product
  6. customwas purified by flash silica gel chromatography (8:2 ethyl acetate-hexane elution)

Sources & evidence

ORD record
ord-0986fc41883e4b2cacc82af5310a4da8
Source dataset
uspto-grants-1993_06
Patent number
US05218115

Reaction notes

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