3-Bromo-2-chloro-5-nitropyridine → 3-Bromo-2-methoxy-5-nitropyridine

HRID 1621869

Reaktionsgleichung

Reaktionsgleichung von HRID 1621869
[Br:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.[CH3:12][O-:13].[Na+]>CO>[Br:1][C:2]1[C:3]([O:13][CH3:12])=[N:4][CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1

Komponenten

4

Edukt 2

HCID 2308893-Bromo-2-chloro-5-nitropyridineHCID 10942334Sodium Methoxide

Produkt 1

HCID 215844513-Bromo-2-methoxy-5-nitropyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

To a cloudy mixture of 3-bromo-2-chloro-5-nitropyridine (Atlantic Scitech, Linden, N.J., 5.10 g, 21.48 mmol) in 50 mL anhydrous methanol at 0° C. (ice/water bath) was added sodium methoxide 5.4 M in methanol (7.96 mL, 43.0 mmol) dropwise by addition funnel. The reaction became clear then a thick precipitate formed. The ice/water bath was removed and the reaction warmed to ambient temperature, quenched with water and sat'd aq. NH4Cl and DCM. The aqueous layer was extracted with DCM 2 times, and the combined organics were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give 3-bromo-2-methoxy-5-nitropyridine (5.07 g, 21.76 mmol, quantitative yield) as a light yellow solid. m/z (ESI, +ve ion) 233 (M+H)+. 1H NMR (400 MHz, CDCl3) δ 9.02 (d, J=2.3 Hz, 1H), 8.63 (d, J=2.5 Hz, 1H), 4.15 (s, 3H).

Aufarbeitung

  1. additiondropwise by addition funnel
  2. customa thick precipitate formed
  3. customThe ice/water bath was removed
  4. customquenched with water
  5. extractionThe aqueous layer was extracted with DCM 2 times
  6. dry with materialthe combined organics were dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-936afebe63944888b759399ba9057560
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772480B2

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