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

HRID 742429Notes

Reaction equation

HRID 742429 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 placed in a 10L three-necked flask equipped with a stirrer, and hydrogen gas was introduced while vigorously stirring. Heat generated as the reaction proceeded, and the reaction temperature was maintained at 60° to 70° C. by introducing hydrogen at such a rate that the hydrogen gas did not discharge from the system. After completion of the reaction, the reaction mixture was heated (60°-70° C.), and the catalyst was separated by filtration. The organic layer of the filtrate was separated and dried over anhydrous magnesium sulfate. The drying agent was separated by filtration, and the solvent was distilled off under reduced pressure to obtain bis(2-chloro-4-fluoro-5-aminophenyl)carbonate as a white solid (1.01Kg, 2.89 mol, 99.6% yield).

Workup

  1. customequipped with a stirrer
  2. temperatureHeat
  3. temperaturethe reaction temperature was maintained at 60° to 70° C.
  4. customAfter completion of the reaction
  5. temperaturethe reaction mixture was heated (60°-70° C.)
  6. customthe catalyst was separated by filtration
  7. customThe organic layer of the filtrate was separated
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe drying agent was separated by filtration
  10. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-6147161dc49b45348c4b31288a7f0a3d
Source dataset
uspto-grants-1996_09
Patent number
US05554581

Reaction notes

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