Phenol → 2-Bromo-6-phenoxypyridine

HRID 2080053노트

반응식

HRID 2080053 반응식
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.[C:9]1([OH:15])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CC(C)([O-])C.[K+].C(OCC)(=O)C>CS(C)=O.O>[Br:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([O:15][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=1

참가 물질

7

반응물 4

HCID 996PhenolHCID 8857Ethyl AcetateHCID 122742,6-DibromopyridineHCID 23665647Potassium tert-butoxide

생성물 1

HCID 8245892-Bromo-6-phenoxypyridine수율 93%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

반응 조건

온도
160 °C

실험 절차

To a solution of 2,6dibromopyridine (20 g, 84.4 mmol) and phenol (7.94 g, 84.4 mmol) in dimethylsulfoxide (200 mL) was added potassium tert-butoxide (9.47 g, 84.4 mmol), and the solution was stirred at 160° C. for 7 hours. The reaction solution was allowed to room temperature, ethyl acetate and water were added for partitioning, the organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was evaporated, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1), and 2-bromo-6-phenoxy-pyridine (19.6, 93%) was obtained as a yellow solid.

후처리

  1. customwas allowed to room temperature
  2. customfor partitioning
  3. washthe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1)

출처 및 근거

ORD 기록
ord-4d8ded05359f457884c6ce9594307d28
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07932272B2

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