Dimethylformamide → 5-Bromo-2-(3-fluorophenoxy)pyridine

HRID 1691094노트

반응식

HRID 1691094 반응식
CN(C)C=O.[F:6][C:7]1[CH:8]=[C:9]([OH:13])[CH:10]=[CH:11][CH:12]=1.[H-].[Na+].Br[C:17]1[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][N:18]=1>O>[Br:23][C:20]1[CH:21]=[CH:22][C:17]([O:13][C:9]2[CH:10]=[CH:11][CH:12]=[C:7]([F:6])[CH:8]=2)=[N:18][CH:19]=1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 97433-FluorophenolHCID 24758Sodium hydrideHCID 693532,5-Dibromopyridine

생성물 1

HCID 592552205-Bromo-2-(3-fluorophenoxy)pyridine수율 110.6%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
0 °C

실험 절차

To an N,N-dimethylformamide (100 mL) solution of 3-fluorophenol (3.30 g, 29.4 mmol) was added sodium hydride (1.41 g, 29.4 mmol, 50% in oil), which was stirred for 10 minutes at 0° C. 2,5-Dibromopyridine (4.64 g, 19.6 mmol) was then added to this mixture at 0° C., followed by 7 hours and 45 minutes of stirring at 110° C. Water was added to the reaction solution at room temperature, which was then extracted with ethyl acetate. The organic layer was separated, washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=3:1) to obtain the title compound (5.81 g, quant.).

후처리

  1. waitfollowed by 7 hours and 45 minutes
  2. stirringof stirring at 110° C
  3. extractionwhich was then extracted with ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with water and saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under a reduced pressure
  9. customthe residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=3:1)

출처 및 근거

ORD 기록
ord-f6282b6103fc412083df9c43e125980b
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08153662B2

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