Sodium borohydride → (3-Bromopyridin-2-yl)methanol

HRID 423182

Reaktionsgleichung

Reaktionsgleichung von HRID 423182
C[O:2][C:3]([C:5]1[C:10]([Br:11])=[CH:9][CH:8]=[CH:7][N:6]=1)=O.[BH4-].[Na+]>CO>[Br:11][C:10]1[C:5]([CH2:3][OH:2])=[N:6][CH:7]=[CH:8][CH:9]=1

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 12828946Methyl 3-bromo-2-pyridinecarboxylate

Produkt 1

HCID 14022521(3-Bromopyridin-2-yl)methanolAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

3-Bromo-pyridine-2-carboxylic acid methyl ester (12.8 g, 59.2 mmol) is dissolved in methanol (150 mL) and cooled to 0° C. To the mixture is added NaBH4 (11.2 g, 296 mmol) in 1.0 g portions. The mixture is warmed to room temperature and stirred for 3 h. The methanol is removed under reduced pressure, AcOEt is added and the solution is washed with saturated, aqueous ammonium chloride and brine. The organic portion is dried over MgSO4, filtered, and concentrated under reduced pressure to yield 6.8 g (62%) of the title compound as a white solid. GCMS m/e 187 [M−H]−.

Aufarbeitung

  1. temperatureThe mixture is warmed to room temperature
  2. customThe methanol is removed under reduced pressure, AcOEt
  3. additionis added
  4. washthe solution is washed with saturated, aqueous ammonium chloride and brine
  5. dry with materialThe organic portion is dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-90478131fd2643e281544e934bd8959d
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101761B2

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