1-Chloro-4-nitrobenzene → p-Fluoronitrobenzene

HRID 1296807Notes

Reaction equation

HRID 1296807 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7](Cl)=[CH:6][CH:5]=1)([O-:3])=[O:2].[F-:11].[K+]>CS(C)=O>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([F:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Conditions

Temperature
170 °C

Procedure

157 g of 4-nitrochlorobenzene, 200 g of dimethylsulfoxide, 62.7 g of potassium fluoride, and 2.49 g of (N,N-dimethylimidazolidino)tetramethyl-guanidinium chloride were placed in a 1 liter four-neck flask equipped with thermometer, anchor stirrer, and reflux condenser with bubble counter. The mixture was heated with stirring to 170° C. and kept at this temperature for 5 hours. The reaction mixture was then cooled to room temperature, water was added at a volumetric ratio of 1:1, the phases that formed were separated, and, from the organic phase, by fractional distillation at reduced pressure, 4-nitrofluorobenzene was obtained in a yield of 96% of theory.

Workup

  1. customequipped with thermometer, anchor stirrer
  2. temperaturereflux condenser
  3. customwith bubble counter
  4. temperatureThe mixture was heated
  5. temperatureThe reaction mixture was then cooled to room temperature
  6. additionwater was added at a volumetric ratio of 1:1
  7. customthe phases that formed
  8. customwere separated
  9. distillationfrom the organic phase, by fractional distillation at reduced pressure

Sources & evidence

ORD record
ord-9f8d4826342d44c8a0370b0c9de2d007
Source dataset
uspto-grants-2007_07
Patent number
US07247733B2

Reaction notes

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