Methanol → (4-Bromo-6-methylpyridin-2-yl)methanol

HRID 2037317Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2037317
[Br:1][C:2]1[CH:7]=[CH:6]N=[C:4]([CH3:8])[CH:3]=1.S(OOS([O-])(=O)=O)([O-])(=O)=O.[NH4+:19].[NH4+].[CH3:21][OH:22]>OS(O)(=O)=O.O>[Br:1][C:2]1[CH:3]=[C:4]([CH3:8])[N:19]=[C:6]([CH2:21][OH:22])[CH:7]=1

Komponenten

6

Edukt 3

HCID 887MethanolHCID 62648Ammonium Persulfate2×HCID 27628354-Bromo-2-methylpyridine

Produkt 1

HCID 67027007(4-Bromo-6-methylpyridin-2-yl)methanol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

To a solution of 4-bromo-2-methyl-pyridine (5.70 g, 32.14 mmol) in methanol (100 mL), H2SO4 (0.3 mL) is added. The mixture is heated to reflux before a solution of ammonium peroxydisulfate (7.33 g, 32.14 mmol) in water (53 mL) is carefully added. The mixture is stirred at reflux for 2 h before two more portions of ammonium peroxydisulfate (2×7.33 g) are added as a sat. aq. solution. Stirring is continued at reflux for 3 h. Methanol is removed under reduced pressure and the remaining solution is diluted with sat. aq. NaHCO3 solution and extracted with EA. The org. extract is dried over MgSO4, filtered and concentrated. The crude product is purified by CC on silica gel eluting with heptane:EA 3:7 to give (4-bromo-6-methyl-pyridin-2-yl)-methanol (1.31 g) as pale yellow solid; LC-MS: tR=0.31 min; [M+1]+=201.96; 1H NMR (CDCl3): δ 2.55 (s, 3H), 3.59 (s br, 1H), 4.72 (s br, 2H), 7.28 (s, 2H).

Aufarbeitung

  1. temperatureThe mixture is heated
  2. additionis carefully added
  3. additionare added as a sat. aq. solution
  4. stirringStirring
  5. temperatureat reflux for 3 h
  6. customMethanol is removed under reduced pressure
  7. additionthe remaining solution is diluted with sat. aq. NaHCO3 solution
  8. extractionextracted with EA
  9. extractionextract
  10. dry with materialis dried over MgSO4
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customThe crude product is purified by CC on silica gel eluting with heptane:EA 3:7

Quellen und Nachweise

ORD-Eintrag
ord-9702d8839d464c0aa005cfb11309ab55
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08575200B2

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