Bis(2-chloro-4-fluoro-5-nitrophenyl)carbonate → Bis(2-chloro-4-fluoro-5-aminophenyl)carbonate

HRID 1198777Notes

Reaction equation

HRID 1198777 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N+:9]([O-])=O)=[CH:4][C:3]=1[O:12][C:13](=[O:26])[O:14][C:15]1[CH:20]=[C:19]([N+:21]([O-])=O)[C:18]([F:24])=[CH:17][C:16]=1[Cl:25].[H][H]>C1(C)C=CC=CC=1.[Pd]>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([NH2:9])=[CH:4][C:3]=1[O:12][C:13](=[O:26])[O:14][C:15]1[CH:20]=[C:19]([NH2:21])[C:18]([F:24])=[CH:17][C:16]=1[Cl:25]

Participants

5

Reactant 2

HCID 14534132Bis(2-chloro-4-fluoro-5-nitrophenyl)carbonateHCID 178418361HCID 178418361, compound3×

Product 1

HCID 15766649Bis(2-chloro-4-fluoro-5-aminophenyl)carbonateYield 71.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Procedure

Bis(2-chloro-4-fluoro-5-nitrophenyl)carbonate (233 g, 0.57 mol), toluene (2300 ml) as a solvent, and 5 % Pd/C (17.4 g) as a catalyst were put in a 5-liter round-bottom flask as equipped with a stirrer, and hydrogen gas was introduced thereinto with vigorously stirring. With progress of the reaction, the reaction system became exothermic. By introduction of hydrogen gas into the reaction system at such a rate that no hydrogen gas leaked out from the system, the reaction temperature was maintained to fall within the range of from 50° to 60° C. After reaction, the reaction mixture was heated (80° to 100° C.), and the used catalyst was taken out therefrom by filtration. The by-produced water was removed form the resulting filtrate, which was fully dried with anhydrous magnesium sulfate. The drying agent was taken out by filtration, and the solvent was removed by distillation under reduced pressure to obtain bis(2-chloro-4-fluoro-5-aminophenyl)carbonate (143 g, 0.41 mol) as a white solid. Yield: 71.9 %.

Workup

  1. customas equipped with a stirrer
  2. customWith progress of the reaction
  3. temperaturethe reaction temperature was maintained
  4. customto fall within the range of from 50° to 60° C
  5. customAfter reaction
  6. temperaturethe reaction mixture was heated (80° to 100° C.)
  7. filtrationby filtration
  8. customThe by-produced water was removed form the resulting filtrate, which
  9. dry with materialwas fully dried with anhydrous magnesium sulfate
  10. filtrationThe drying agent was taken out by filtration
  11. customthe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-aac9b15e9a1b42b0ac337234d6fac5bb
Source dataset
uspto-grants-1994_01
Patent number
US05281742

Reaction notes

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