2-Benzyloxy-5-nitroiodobenzene → 4-(Benzyloxy)-3-iodobenzenamine

HRID 565379노트

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HRID 565379 반응식
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][C:10]=1[I:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O.C(O)(=O)C.[Fe]>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][C:10]=1[I:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 1

HCID 226181932-Benzyloxy-5-nitroiodobenzene

생성물 1

HCID 226181994-(Benzyloxy)-3-iodobenzenamine수율 99%

시약·촉매·용매 3

HCID 23925Iron촉매HCID 176Acetic Acid용매HCID 962Water용매

반응 조건

온도
80 °C

실험 절차

Iron powder (12.5 g, 224 mmol) was added to a suspension of 2-benzyloxy-5-nitroiodobenzene (Description 13; 10 g, 28 mmol) in water (300 ml) and acetic acid (75 ml) and the mixture was stirred at 80° C. for 12 hours. The mixture was allowed to cool to room temperature and filtered through Hyflo™, washing with 4:1 water:acetic acid and ethyl acetate. The filtrate was extracted with ethyl acetate, and the organic extract was evaporated under reduced pressure. Saturated aqueous sodium hydrogen carbonate was added and the mixture was extracted with ethyl acetate. The organic extract was washed with brine, dried (MgSO4), and the solvent was evaporated under reduced pressure to give the title compound as a brown oil (9 g, 99% yield). 1H NMR (360 MHz, CDCl3) δ 7.49−7.47 (2H, m), 7.40−7.28 (3H, m), 7.19 (1H, d, J 2.4 Hz), 6.70 (1H, d, J 8.6 Hz), 6.62 (1H, dd, J 2.4, 8.6 Hz), and 5.04 (2H, s). m/z (ES+) 326 (M+1)+.

후처리

  1. temperatureto cool to room temperature
  2. filtrationfiltered through Hyflo™
  3. washwashing with 4:1 water
  4. extractionThe filtrate was extracted with ethyl acetate
  5. extractionthe organic extract
  6. customwas evaporated under reduced pressure
  7. additionSaturated aqueous sodium hydrogen carbonate was added
  8. extractionthe mixture was extracted with ethyl acetate
  9. extractionThe organic extract
  10. washwas washed with brine
  11. dry with materialdried (MgSO4)
  12. customthe solvent was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-5f26c52a30024988b632e1744e62b7be
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06172077B2

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