Water → 1-Fluoro-3-(4-fluorophenoxy)-5-nitrobenzene

HRID 873489Notes

Reaction equation

HRID 873489 reaction equation
F[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([F:11])[CH:3]=1.[C:12](=[O:15])([O-])[O-].[Cs+].[Cs+].O>FC1C=CC(O)=CC=1.CC(N(C)C)=O.C(OCC)(=O)C>[F:11][C:4]1[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=[C:2]([O:15][C:12]2[CH:6]=[CH:5][C:4]([F:11])=[CH:3][CH:2]=2)[CH:3]=1

Participants

7

Reactant 3

HCID 962WaterHCID 10796Cesium carbonateHCID 752721,3-Difluoro-5-nitrobenzene

Product 1

HCID 807530011-Fluoro-3-(4-fluorophenoxy)-5-nitrobenzeneYield 296.7%

Reagents, catalysts & solvents 3

HCID 8857Ethyl AcetateSolventHCID 97324-FluorophenolSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
50 °C

Procedure

Under an argon atmosphere and at room temperature, in a 500-mL pear-shaped evaporating flask, 4-fluorophenol (18.5 g) and 1,3-difluoro-5-nitrobenzene (25.0 g) were dissolved in DMA (300 mL). The reaction system was added with cesium carbonate (15.3 g) and stirred. The reaction system was then heated to 50° C., stirred for 3 hours, then heated to 65° C., stirred for 1 hour and further heated to 85° C. and stirred for 1 hour. The reaction solution was allowed to cool to room temperature, diluted with ethyl acetate and added with water to extract an organic layer. The aqueous layer was added with ethyl acetate to extract an organic layer. The organic layer was combined and washed with water and a saturated sodium chloride solution and the solvent was then distilled off under reduced pressure to give the titled compound (35.0 g) having the following physical properties.

Workup

  1. stirringstirred for 3 hours
  2. temperatureheated to 65° C.
  3. stirringstirred for 1 hour
  4. temperaturefurther heated to 85° C.
  5. stirringstirred for 1 hour
  6. temperatureto cool to room temperature
  7. extractionto extract an organic layer
  8. additionThe aqueous layer was added with ethyl acetate
  9. extractionto extract an organic layer
  10. washwashed with water
  11. distillationa saturated sodium chloride solution and the solvent was then distilled off under reduced pressure

Sources & evidence

ORD record
ord-7fb95b2de49743158afa66e2a1eeb7d0
Source dataset
uspto-grants-2015_03
Patent number
US08975409B2

Reaction notes

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