2-Bromo-5-iodo-3-methylpyridine → 5-Iodo-2-methoxy-3-methylpyridine

HRID 1432874

Reaktionsgleichung

Reaktionsgleichung von HRID 1432874
Br[C:2]1[C:7]([CH3:8])=[CH:6][C:5]([I:9])=[CH:4][N:3]=1.[CH3:10][O-:11].[Na+]>CS(C)=O.C(OCC)C.O>[I:9][C:5]1[CH:6]=[C:7]([CH3:8])[C:2]([O:11][CH3:10])=[N:3][CH:4]=1

Komponenten

6

Edukt 2

HCID 101086802-Bromo-5-iodo-3-methylpyridineHCID 10942334Sodium Methoxide

Produkt 1

HCID 534159905-Iodo-2-methoxy-3-methylpyridineAusbeute 71,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a solution containing 2-bromo-5-iodo-3-methyl-pyridine (4.80 g, 16.0 mmol) in DMSO (15 mL) is added methanolic NaOMe (3.33 M, 5.3 mL, 17.7 mmol) at 0° C. The solution is allowed to warm to ambient temperature and then heated at 70° C. for 1 hour. The reaction mixture is diluted with diethyl ether (300 mL) and water (200 mL) and the layers are separated. The organic phase is washed with brine, dried over anhydrous Na2SO4, filtered and concentrated. The crude product is purified by silica gel flash column chromatography (hexane/diethyl ether, 19:1) to provide 2.86 g (71%) of the title compound as a white solid. 1H NMR (300 MHz, CDCl3) δ2.12 (s, 3H), 3.90 (s, 3H), 7.60 (d, J=2.1 Hz, 1H), 8.14 (d, J=2.1 Hz, 1H) ppm; MS (EI): m/z 249 (M+).

Aufarbeitung

  1. temperatureheated at 70° C. for 1 hour
  2. customthe layers are separated
  3. washThe organic phase is washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product is purified by silica gel flash column chromatography (hexane/diethyl ether, 19:1)

Quellen und Nachweise

ORD-Eintrag
ord-1e6d615f5fbe42699a7390bfa217cf1d
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07612075B2

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