Trifluoroacetic anhydride → (3-Bromo-5-fluoro-4-methyl-2-pyridyl)methanol

HRID 468948노트

반응식

HRID 468948 반응식
FC(F)(F)C(O[C:6](=[O:11])[C:7](F)(F)F)=O.[Br:14][C:15]1C(C)=[N+:17]([O-])[CH:18]=[C:19]([F:22])[C:20]=1[CH3:21]>C(Cl)Cl.C(OCC)(=O)C>[Br:14][C:15]1[C:7]([CH2:6][OH:11])=[N:17][CH:18]=[C:19]([F:22])[C:20]=1[CH3:21]

참가 물질

5

반응물 2

HCID 9845Trifluoroacetic anhydrideHCID 679750773-Bromo-5-fluoro-2,4-dimethylpyridine 1-oxide

생성물 1

HCID 67974745(3-Bromo-5-fluoro-4-methyl-2-pyridyl)methanol수율 68.2%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

Trifluoroacetic anhydride (0.35 mL, 2.5 mmol) was added dropwise to a solution of 3-bromo-5-fluoro-2,4-dimethylpyridine 1-oxide (220 mg; 1.0 mmol) in DCM (3 mL). The reaction mixture was stirred at room temperature overnight and then diluted with ethyl acetate (50 mL) and washed with saturated aqueous sodium bicarbonate solution (20 mL). The organic layer was separated, dried over sodium sulfate, filtered and concentrated in vacuo to provide a residue that was purified by flash chromatography (4 g, Silica, 0-100% ethyl acetate in heptane). Desired fractions were combined and evaporated in vacuo to afford the title compound as a pale yellow oil (150 mg, 68%), which was used in the next step without further purification.

후처리

  1. washwashed with saturated aqueous sodium bicarbonate solution (20 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto provide a residue that
  7. customwas purified by flash chromatography (4 g, Silica, 0-100% ethyl acetate in heptane)
  8. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-00c81742f5db4f639c168ab2934dd2a6
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08623889B2

반응 노트

불러오는 중…