Sodium Hydroxide → 4-Bromo-2,5-dimethylpyridine

HRID 708577노트

반응식

HRID 708577 반응식
[CH3:1][C:2]1[CH:7]=[C:6]([N+]([O-])=O)[C:5]([CH3:11])=[CH:4][N+:3]=1[O-].P(Br)(Br)[Br:14].[OH-].[Na+]>CCOC(C)=O>[Br:14][C:6]1[C:5]([CH3:11])=[CH:4][N:3]=[C:2]([CH3:1])[CH:7]=1

참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 24614Phosphorus tribromideHCID 146707Pyridine, 2,5-dimethyl-4-nitro-, 1-oxide

생성물 1

HCID 223175304-Bromo-2,5-dimethylpyridine

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매2회

실험 절차

Bromination. To a solution of 1.65 g of 2,5-dimethyl-4-nitro-pyridine 1-oxide in 50 mL dry EtOAc was added 11.1 mL PBr3 at rt. The mixture was heated to reflux over 0.5 h. Reflux continued for 3 h, then cooled to rt and poured into ice and EtOAc. The resulting mixture was brought to pH 10 with addition of NaOH pellets and layers were separated. An additional EtOAc extraction was combined with the first and the organic layers were washed with brine, dried whith Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (hexanes-EtOAc) to provide 4-bromo-2,5-dimethyl-pyridine (248 mg). LCMS (m/z) 186.

후처리

  1. temperatureThe mixture was heated
  2. temperatureto reflux over 0.5 h
  3. temperatureReflux
  4. customwere separated
  5. extractionAn additional EtOAc extraction
  6. washwere washed with brine
  7. dry with materialdried whith Na2SO4
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by column chromatography (hexanes-EtOAc)

출처 및 근거

ORD 기록
ord-800e3c6d2f224f20855d8bd59c17d68a
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09175003B2

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