Water → Nitrofen

HRID 2237023Notes

Reaction equation

HRID 2237023 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:17][C:18]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:19]=1[OH:25].O>CN(C=O)C>[Cl:17][C:18]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:19]=1[O:25][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 84492,4-DichlorophenolHCID 9590p-FluoronitrobenzeneHCID 11430Potassium Carbonate

Product 1

HCID 15787Nitrofen

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 1-fluoro-4-nitrobenzene (10 mmol) in DMF (20 mL) at rt, solid potassium carbonate (30 mmol) was added followed by addition of 2,4-dichlorophenol (10 mmol) to the reaction mixture and heating to 80° C. until the reaction was complete as indicated by TLC or HPLC. After cooling to rt, the reaction mixture was poured into H2O (100 ml), extracted with EtOAc (2×50 mL), washed with H2O (2×50 ml) and brine (50 ml), and dried over sodium sulfate. The solvent was removed in vacuuo to afford the desired 4-(2,4-dichloro-phenoxy)-1-nitrobenzene. The crude product was used for further transformation .

Workup

  1. temperatureAfter cooling to rt
  2. extractionextracted with EtOAc (2×50 mL)
  3. washwashed with H2O (2×50 ml) and brine (50 ml)
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was removed in vacuuo

Sources & evidence

ORD record
ord-efeee33df957445abeac0e2373aeede8
Source dataset
uspto-grants-2010_05
Patent number
US07714013B2

Reaction notes

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