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

HRID 275095Notes

Reaction equation

HRID 275095 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 99.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Procedure

Bis(2-chloro-4-fluoro-5-nitrophenyl)carbonate (1.2 kg, 2.9 mol), toluene (7 liters) as a solvent, and 5% Pd/C (200 g) as a catalyst were put in a 10-liter three-neck 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 60° to 70° C. After reaction, the reaction mixture was heated (60° to 70° C.), and the used catalyst was taken out therefrom by filtration. The organic layer of the resulting filtrate was separated and was 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 (1.01 kg, 2.89 mol) as a white solid. Yield: 99.6%. Melting point, 1H NMR spectral data and IR spectral data of the product were same as those in Example 7.

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 60° to 70° C
  5. customAfter reaction
  6. temperaturethe reaction mixture was heated (60° to 70° C.)
  7. filtrationby filtration
  8. customThe organic layer of the resulting filtrate was separated
  9. dry with materialwas 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-1279cb1c26e34a67a3505748bcd61520
Source dataset
uspto-grants-1995_02
Patent number
US05391807

Reaction notes

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