1,2,4,5-Tetrafluoro-3-methoxy-6-nitrobenzene → 4-Methoxy-2-phthalimido-3,5,6-trifluoro-1-nitrobenzene

HRID 358868Notes

Reaction equation

HRID 358868 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].[CH3:13][O:14][C:15]1[C:20]([F:21])=[C:19](F)[C:18]([N+:23]([O-:25])=[O:24])=[C:17]([F:26])[C:16]=1[F:27]>CN(C)C=O>[CH3:13][O:14][C:15]1[C:16]([F:27])=[C:17]([F:26])[C:18]([N+:23]([O-:25])=[O:24])=[C:19]([N:5]2[C:1](=[O:11])[C:2]3=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]3[C:4]2=[O:6])[C:20]=1[F:21]

Participants

4

Reactant 2

HCID 42613721,2,4,5-Tetrafluoro-3-methoxy-6-nitrobenzeneHCID 24194345Phthalimide potassium salt

Product 1

HCID 200671344-Methoxy-2-phthalimido-3,5,6-trifluoro-1-nitrobenzeneYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4.62 g (0.025 mole) of potassium phthalimide were added to a solution of 5.41 g (0.024 mole) of 4-methoxy-2,3,5,6-tetrafluoro-1-nitrobenzene (XXXIII) in 100 ml of dimethylformamide, and the mixture was stirred at room temperature for 3 hours. At the end of this time, the solvent was removed by evaporation under reduced pressure, the residue was dissolved in toluene, and the solution was washed with water, dried and concentrated by evaporation under reduced pressure to give an oily substance. This oily substance was subjected to silica gel column chromatography eluted with toluene, to afford 5.07 g of 4-methoxy-2-phthalimido-3,5,6-trifluoro-1-nitrobenzene (XXXIV) as pale yellow powdery crystals.

Workup

  1. customAt the end of this time, the solvent was removed by evaporation under reduced pressure
  2. dissolutionthe residue was dissolved in toluene
  3. washthe solution was washed with water
  4. customdried
  5. concentrationconcentrated by evaporation under reduced pressure
  6. customto give an oily substance
  7. washeluted with toluene

Sources & evidence

ORD record
ord-aadd31a63e784190b9647379efa783e7
Source dataset
uspto-grants-1991_03
Patent number
US04997943

Reaction notes

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