Sodium Dithionite → 4-Bromo-2-(2,2-dimethoxyethyl)aniline

HRID 1668460노트

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HRID 1668460 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[C:4]([CH2:11][CH:12]([O:15][CH3:16])[O:13][CH3:14])[CH:3]=1.S(S([O-])=O)([O-])=O.[Na+].[Na+].C(=O)(O)[O-].[Na+]>C(O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([CH2:11][CH:12]([O:15][CH3:16])[O:13][CH3:14])[CH:3]=1

참가 물질

5

반응물 3

HCID 24489Sodium DithioniteHCID 516892Sodium BicarbonateHCID 590046464-Bromo-2-(2,2-dimethoxyethyl)-1-nitrobenzene

생성물 1

HCID 590046094-Bromo-2-(2,2-dimethoxyethyl)aniline수율 47.5%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

Compound 66 (75 mg, 0.259 mmol) was dissolved in anhydrous ethanol (10 mL) in a dry argon purged flask fitted with a magnetic stir bar and condenser. Sodium dithionite (158.8 mg, 0.776 mmol) and sodium bicarbonate (130.6 mg, 1.554 mmol) are added to the flask and mixture heated to reflux for 24 hours. After cooling to room temperature, the reaction was quenched by the addition of H2O (10 mL) and the ethanol removed under reduced pressure. The resulting aqueous layer was transferred to a separatory funnel and extracted with ethyl acetate (three times). The combined organic layers were washed with brine, dried over sodium sulphate, filtered, concentrated and the residue purified via chromatography on silica gel (methanol:CH2Cl2, 2:98) to yield a brown oil, 67 (32 mg, 47.5%). 1H NMR (CDCl3) δ 2.83 (d, 2H, J=5.3 Hz), 3.38 (s, 6H), 4.48 (t, 1H, J=5.3 Hz), 6.61 (d, 1H, J=8.2 Hz), 7.13 (d, 1H, J=2.2 Hz), 7.15-7.17 (m, 1H); ESI-MS (m/z, %): 198/200 (M+−2MeO, 100%).

후처리

  1. customfitted with a magnetic stir bar and condenser
  2. temperatureheated
  3. temperatureto reflux for 24 hours
  4. customthe reaction was quenched by the addition of H2O (10 mL)
  5. customthe ethanol removed under reduced pressure
  6. customThe resulting aqueous layer was transferred to a separatory funnel
  7. extractionextracted with ethyl acetate (three times)
  8. washThe combined organic layers were washed with brine
  9. dry with materialdried over sodium sulphate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customthe residue purified via chromatography on silica gel (methanol:CH2Cl2, 2:98)

출처 및 근거

ORD 기록
ord-945e3c0d470244abbf24c862108876e9
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07989447B2

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