4-Chlorophenol → 1-Chloro-4-(4-nitrophenoxy)benzene

HRID 35688

Reaction equation

HRID 35688 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 46844-ChlorophenolHCID 9590p-FluoronitrobenzeneHCID 11430Potassium Carbonate

Product 1

HCID 157861-Chloro-4-(4-nitrophenoxy)benzeneYield 702.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

Under a dry nitrogen atmosphere a stirred mixture of 10.9 g (0.077 mole) 4-fluoronitrobenzene, 9.95 g (0.0077 mole) 4-chlorophenol, and 11.8 g (0.085 mole) potassium carbonate in 175 mL of dimethylsulfoxide was heated at 70° C. for two days. The reaction mixture was cooled and filtered. The filtrate was diluted with water until a volume of one liter was obtained. This mixture was extracted with three 200 mL portions of diethyl ether. The combined ether extract was washed with water followed by an aqueous saturated sodium chloride solution. The washed extract was dried over anhydrous sodium sulfate and filtered. Evaporation of the filtrate under reduced pressure yielded 13.5 g 4-(4-chlorophenoxy)nitrobenzene (mp 67°-70° C.).

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered
  3. additionThe filtrate was diluted with water until a volume of one liter
  4. customwas obtained
  5. extractionThis mixture was extracted with three 200 mL portions of diethyl ether
  6. extractionThe combined ether extract
  7. washwas washed with water
  8. extractionThe washed extract
  9. dry with materialwas dried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. customEvaporation of the filtrate under reduced pressure

Sources & evidence

ORD record
ord-c1a9a8715b9a4c9ebcfe2d77541c3e8e
Source dataset
uspto-grants-1988_08
Patent number
US04767779

Linked notes

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