N-bromobutanimide → 3-Bromo-2-fluoro-6-(neopentyloxy)pyridine

HRID 455696

반응식

HRID 455696 반응식
[Br:1]N1C(=O)CCC1=O.[F:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])[N:11]=1>C(#N)C>[Br:1][C:15]1[C:10]([F:9])=[N:11][C:12]([O:16][CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:13][CH:14]=1

참가 물질

4

반응물 2

HCID 67184N-bromobutanimideHCID 574756582-Fluoro-6-(neopentyloxy)pyridine

생성물 1

HCID 574756593-Bromo-2-fluoro-6-(neopentyloxy)pyridine수율 51.8%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
70 °C

실험 절차

N-bromosuccinimide (8.29 g, 46.6 mmol) was added to a solution of 2-fluoro-6-(neopentyloxy)pyridine (7.11 g, 38.8 mmol) in acetonitrile (80 mL) at rt. The reaction mixture was heated to 70° C. overnight. The reaction mixture was cooled to rt and the solvent was removed under reduced pressure. The residue was dissolved in DCM and washed with water. The organic layer was separated, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography (100% hexanes) to obtain 3-bromo-2-fluoro-6-(neopentyloxy)pyridine (5.27 g, 20.11 mmol) as a white solid.

후처리

  1. temperatureThe reaction mixture was cooled to rt
  2. customthe solvent was removed under reduced pressure
  3. dissolutionThe residue was dissolved in DCM
  4. washwashed with water
  5. customThe organic layer was separated
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash chromatography (100% hexanes)

출처 및 근거

ORD 기록
ord-4d5c88843d5f4cb193de66352cd81375
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08497264B2

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