Water → Benzene, 4-chloro-1-nitro-2-phenoxy-

HRID 1496958Notes

Reaction equation

HRID 1496958 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4](F)[CH:3]=1.[C:12]1([OH:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O.C(OCC)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([O:18][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 996PhenolHCID 11430Potassium CarbonateHCID 696914-Chloro-2-fluoro-1-nitrobenzene

Product 1

HCID 12290044Benzene, 4-chloro-1-nitro-2-phenoxy-

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolvent

Procedure

4-chloro-2-fluoro-nitrobenzene (500 mg), phenol (270 mg), and potassium carbonate (400 mg) were dissolved in dimethyl sulfoxide (10 ml), and stirred at room temperature for 2 hours. The mixture was added with water and ethyl ether to extract an organic layer. The resulting organic layer was washed with saturated brine, and water was removed with sodium sulfate, and the solvent was removed by distillation under reduced pressure. The yellow target compound obtained by removing the solvent was used in the subsequent reaction without further purification (500 mg).

Workup

  1. extractionto extract an organic layer
  2. washThe resulting organic layer was washed with saturated brine, and water
  3. customwas removed with sodium sulfate
  4. customthe solvent was removed by distillation under reduced pressure
  5. customThe yellow target compound obtained
  6. customby removing the solvent
  7. customwas used in the subsequent reaction without further purification (500 mg)

Sources & evidence

ORD record
ord-0ab8e1930a96477aa8d4a839d683cd10
Source dataset
uspto-grants-2015_12
Patent number
US09199944B2

Reaction notes

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