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

HRID 1198778노트

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HRID 1198778 반응식
[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]

참가 물질

5

반응물 2

HCID 14534132Bis(2-chloro-4-fluoro-5-nitrophenyl)carbonateHCID 178418361HCID 178418361, 화합물3회

생성물 1

HCID 15766649Bis(2-chloro-4-fluoro-5-aminophenyl)carbonate수율 99.7%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-71b0dfb81cfd430aad1fb65272a08582
출처 데이터셋
uspto-grants-1994_01
특허 번호
US05281742

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