Phenol → 1-Nitro-4-phenoxybenzene

HRID 726919Notes

Reaction equation

HRID 726919 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[C:11]1([OH:17])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C([O-])([O-])=O.[K+].[K+].C(OCC)(=O)C>CN(C)C=O.O>[O:17]([C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 996PhenolHCID 8857Ethyl AcetateHCID 9590p-FluoronitrobenzeneHCID 11430Potassium Carbonate

Product 1

HCID 121101-Nitro-4-phenoxybenzene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4-fluoronitrobenzene (0.50 mL) and phenol (443 mg) in 5.0 mL of dimethylformamide was added K2CO3 (1.27 g). The reaction was warmed to 70° C. for 20 h, then cooled to room temperature and poured into ethyl acetate and water. The organic layer was washed with water, sat. aq. NaHCO3 solution, and brine. The solution was dried (Na2SO4), filtered, and concentrated in vacuo to provide the crude product as a yellow solid.

Workup

  1. temperaturecooled to room temperature
  2. washThe organic layer was washed with water, sat. aq. NaHCO3 solution, and brine
  3. dry with materialThe solution was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b62a27e8eec645568e79bbfd4133ff37
Source dataset
uspto-grants-1998_01
Patent number
US05710171

Reaction notes

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