Phosphorus oxychloride → 2-Chloro-6-(2-methoxy-4-trifluoromethoxy-phenyl)-5-methyl-3-nitro-pyridine

HRID 2179998노트

반응식

HRID 2179998 반응식
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][C:10]([F:13])([F:12])[F:11])[CH:6]=[CH:5][C:4]=1[C:14]1[C:19]([CH3:20])=[CH:18][C:17]([N+:21]([O-:23])=[O:22])=[CH:16][N+:15]=1[O-].O=P(Cl)(Cl)[Cl:27]>>[Cl:27][C:16]1[C:17]([N+:21]([O-:23])=[O:22])=[CH:18][C:19]([CH3:20])=[C:14]([C:4]2[CH:5]=[CH:6][C:7]([O:9][C:10]([F:13])([F:12])[F:11])=[CH:8][C:3]=2[O:2][CH3:1])[N:15]=1

참가 물질

3

반응물 2

HCID 24813Phosphorus oxychlorideHCID 224900552-(2-Methoxy-4-trifluoromethoxy-phenyl)-3-methyl-5-nitro-pyridine 1-oxide

생성물 1

HCID 224900592-Chloro-6-(2-methoxy-4-trifluoromethoxy-phenyl)-5-methyl-3-nitro-pyridine

반응 조건

온도
75 °C

실험 절차

POCl3 (500 ml) is added to 2-(2-methoxy-4-trifluoromethoxy-phenyl)-3-methyl-5-nitro-pyridine 1-oxide (97 g, 0.3 mol) at room temperature and the mixture is stirred at 75° C. for 2 hours. The mixture is concentrated under reduced pressure. Aqueous saturated Na2CO3 is added to the residue and the mixture is extracted with EtOAc. The combined extracts are washed with brine and dried over Na2SO4. The solvent is removed under reduced pressure. The residue is purified by flash column chromatography (hexane/EtOAc 10:1) to obtain 2-chloro-6-(2-methoxy-4-trifluoromethoxy-phenyl)-5-methyl-3-nitro-pyridine. Rf (hexane/EtOAc=9:1)=0.35.

후처리

  1. concentrationThe mixture is concentrated under reduced pressure
  2. additionAqueous saturated Na2CO3 is added to the residue
  3. extractionthe mixture is extracted with EtOAc
  4. washThe combined extracts are washed with brine
  5. dry with materialdried over Na2SO4
  6. customThe solvent is removed under reduced pressure
  7. customThe residue is purified by flash column chromatography (hexane/EtOAc 10:1)

출처 및 근거

ORD 기록
ord-194a9a9eb48b41f7be350ef8622f3297
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06887875B2

반응 노트

불러오는 중…