Dimethylformamide → 5-Bromo-2-(4-fluorophenoxy)pyridine

HRID 640291노트

반응식

HRID 640291 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Br[C:10]1[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][N:11]=1.CN(C)C=O.[H-].[Na+]>O>[Br:16][C:13]1[CH:14]=[CH:15][C:10]([O:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[N:11][CH:12]=1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 97324-FluorophenolHCID 24758Sodium hydrideHCID 693532,5-Dibromopyridine

생성물 1

HCID 574253025-Bromo-2-(4-fluorophenoxy)pyridine수율 75%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a mixture of 4-fluorophenol (2.1 g, 19 mmol), 2,5-dibromopyridine (3.0 g, 13 mmol) and N,N-dimethylformamide (30 mL) was added sodium hydride (730 mg, 15 mmol, 50% in oil) at 0° C., which was stirred for 10 minutes at room temperature. The reaction mixture was then stirred for 5 hours at 110° C. The reaction mixture was cooled to room temperature and water was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with water twice, and then washed with saturated aqueous sodium chloride, and was concentrated under a reduced pressure, and the residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=15:1) to obtain the title compound (2.6 g, 75%).

후처리

  1. stirringThe reaction mixture was then stirred for 5 hours at 110° C
  2. temperatureThe reaction mixture was cooled to room temperature
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with water twice
  5. washwashed with saturated aqueous sodium chloride
  6. concentrationwas concentrated under a reduced pressure
  7. customthe residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=15:1)

출처 및 근거

ORD 기록
ord-d99e3248a1d8464e92be6a5a0f5bc5a0
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07691882B2

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