Water → HCID 15480990, compound

HRID 1275682Notes

Reaction equation

HRID 1275682 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=1[F:17])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1.CC(C)([O-])C.[K+].F[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[N+:31]([O-:33])=[O:32].O>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=1[F:17])[CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[N+:31]([O-:33])=[O:32])=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 738951-Fluoro-2-nitrobenzeneHCID 15480989HCID 15480989, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 15480990HCID 15480990, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(3,4-difluorobenzyloxy)phenol (1.00 g, 4.2 mmol) in N,N-dimethylformamide (20 ml) was added potassium tert-butoxide (0.47 g, 4.2 mmol), followed by stirring at room temperature for 30 minutes. To the reaction solution was added 1-fluoro-2-nitrobenzene (0.60 g, 4.3 mmol), followed by stirring at 150° C. for 5 hours. After allowing to stand overnight, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium chloride solution and dried. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent; chloroform) to give 1-[4-(3,4-difluorobenzyloxy)phenoxy]-2-nitrobenzene (1.41 g).

Workup

  1. stirringby stirring at 150° C. for 5 hours
  2. waitto stand overnight
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materiala saturated aqueous sodium chloride solution and dried
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (eluent; chloroform)

Sources & evidence

ORD record
ord-edbdc39de375476284200a36db7bf758
Source dataset
uspto-grants-2000_12
Patent number
US06162832

Reaction notes

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