Dimethylformamide → 5-Bromo-2-chloro-3-nitropyridine

HRID 1485517

반응식

HRID 1485517 반응식
[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5](=O)[NH:6][CH:7]=1.CN(C=O)C.O=P(Cl)(Cl)[Cl:19]>>[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5]([Cl:19])=[N:6][CH:7]=1

참가 물질

4

반응물 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 851475-Bromo-3-nitro-2-pyridone

생성물 1

HCID 70194125-Bromo-2-chloro-3-nitropyridine수율 85%

실험 절차

To a solution of 5-bromo-3-nitropyridin-2(1H)-one (4.62 g, 21.10 mmol) in POCl3 (46.2 ml) was added DMF (4.62 ml, 59.7 mmol) at room temperature. The mixture was refluxed for 2 hours, and then cooled to room temperature and concentrated in vacuo. The residue was treated with saturated aq. NaHCO3 and extracted with EtOAc. The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography on SiO2 (Hex:EtOAc=3:1) to give 5-bromo-2-chloro-3-nitropyridine (4.24 g, 85%) as a yellow solid. 1H-NMR (CDCl3, Varian 400 MHz) δ 8.37 (1H, d, J=2.4 Hz), 8.70 (1H, d, J=2.0 Hz).

후처리

  1. temperatureThe mixture was refluxed for 2 hours
  2. concentrationconcentrated in vacuo
  3. additionThe residue was treated with saturated aq. NaHCO3
  4. extractionextracted with EtOAc
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by column chromatography on SiO2 (Hex:EtOAc=3:1)

출처 및 근거

ORD 기록
ord-ac60d0e5e6884b69b696ccae93017adc
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09422298B2

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