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

HRID 455696

Reaktionsgleichung

Reaktionsgleichung von HRID 455696
[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

Komponenten

4

Edukt 2

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

Produkt 1

HCID 574756593-Bromo-2-fluoro-6-(neopentyloxy)pyridineAusbeute 51,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-4d5c88843d5f4cb193de66352cd81375
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08497264B2

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