2,2,2-Trifluoroethanol → 3-Bromo-5-(2,2,2-trifluoroethoxy)pyridine

HRID 24050노트

반응식

HRID 24050 반응식
[H-].[Na+].[F:3][C:4]([F:8])([F:7])[CH2:5][OH:6].[Br:9][C:10]1[CH:11]=[N:12][CH:13]=[C:14](Br)[CH:15]=1>CN(C=O)C.O>[Br:9][C:10]1[CH:11]=[N:12][CH:13]=[C:14]([O:6][CH2:5][C:4]([F:8])([F:7])[F:3])[CH:15]=1

참가 물질

6

반응물 3

HCID 64092,2,2-TrifluoroethanolHCID 24758Sodium hydrideHCID 693693,5-Dibromopyridine

생성물 1

HCID 225703523-Bromo-5-(2,2,2-trifluoroethoxy)pyridine수율 46%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매2회

반응 조건

온도
70 °C

실험 절차

To a slurry of sodium hydride (60% dispersion in mineral oil, 0.54 g, 14 mmol) in DMF (15 mL) was added commercially available 2,2,2-trifluoroethanol (0.97 mL, 14 mmol) at room temperature. After stirring for 15 minutes, a solution of 3,5-dibromopyridine (3.2 g, 14 mmol) in 5 mL of DMF was added dropwise. The reaction mixture was heated overnight at 70° C. After cooling to room temperature, the reaction was diluted with water and extracted with ethyl acetate. The extracts were dried over magnesium sulfate and the solvent was removed under reduced pressure. The crude product was chromatographed on silica (5% ethyl acetate/hexanes) to give the title compound (1.6 g, 46% yield) as clear oil. 1H NMR (CDCl3) δ 8.42 (d, 1H, J=1.7 Hz), 8.32 (d, 1H, J=2.5 Hz), 7.46 (m, 1H), 4.42 (m, 2H).

후처리

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extracts were dried over magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe crude product was chromatographed on silica (5% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-846bceea113f4a91acc8e987af3cd9ec
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06855722B2

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