Sodium Carbonate → 4-Bromo-3-chlorobenzene-1,2-diamine

HRID 913564노트

반응식

HRID 913564 반응식
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-])=O)[C:3]=1[Cl:12].C([O-])([O-])=O.[Na+].[Na+]>CCO.O>[Br:1][C:2]1[C:3]([Cl:12])=[C:4]([NH2:9])[C:5]([NH2:6])=[CH:7][CH:8]=1

참가 물질

5

반응물 2

HCID 10340Sodium CarbonateHCID 265991564-Bromo-3-chloro-2-nitroaniline

생성물 1

HCID 578001544-Bromo-3-chlorobenzene-1,2-diamine수율 96.3%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

To a stirred solution of 4-bromo-3-chloro-2-nitroaniline (0.200 g, 0.797 mmol) in EtOH (100 mL), was added SnCl2-2H2O (0.9 g, 3.985 mmol). The reaction mixture was heated to reflux for 3.5 h. The cooled solution (to rt) was diluted with H2O and the pH was adjusted to ca. 10 with Na2CO3. Extraction with CHCl3 (×3), was followed by washing with brine, drying over Na2SO4, and filtration. Concentration afforded an orange solid that was dried under vacuum to obtain 0.17 g product: 1H NMR (400 MHz, CDCl3) δ 6.92 (d, J=8.4 Hz, 1H), 6.51 (d, J=8.4 Hz, 1H), 3.90 (s, 2H), 3.40 (s, 2H); MS (ESI) m/z 223 (M+1).

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 3.5 h
  3. extractionExtraction with CHCl3 (×3)
  4. washby washing with brine
  5. dry with materialdrying over Na2SO4, and filtration
  6. concentrationConcentration
  7. customafforded an orange solid
  8. customthat was dried under vacuum

출처 및 근거

ORD 기록
ord-e6a1289e03824bbaaddea45adad8311d
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08026262B2

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