Methanol → 2,6-Dinitrophenyl methyl ether

HRID 1501875

Reaktionsgleichung

Reaktionsgleichung von HRID 1501875
Br[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[CH3:14][OH:15]>>[CH3:14][O:15][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Komponenten

3

Edukt 2

HCID 887MethanolHCID 138024382-Bromo-1,3-dinitrobenzene

Produkt 1

HCID 5977192,6-Dinitrophenyl methyl ether

Versuchsvorschrift

An argon filled Schlenk flask was charged with 25.77 g (104 mmol) of 2-bromo-1,3-dinitrobenzene, 150 mL of absolute methanol was added and the reaction mixture was chilled in an ice bath. 2.4 g (104 mmol) of Na was added, and the resulting reaction mixture was purged with argon until all Na was dissolved and stirred at RT over night. The solvent was removed, the residue was re-suspended in acetone and filtered through Celite to remove NaBr. The solvent was removed, and the crude product was recrystallized from iPrOH. Yield: 19.8 g (90%). 1H NMR (CDCl3): δ 8.05 (d, JHH=8.2 Hz, 2H, Ar), 7.38 (t, JHH=8.2 Hz, 1H, Ar), 4.07 (s, 3H, OCH3) ppm.

Aufarbeitung

  1. additionwas added
  2. temperaturethe reaction mixture was chilled in an ice bath
  3. customthe resulting reaction mixture
  4. customwas purged with argon until all Na
  5. dissolutionwas dissolved
  6. customThe solvent was removed
  7. filtrationfiltered through Celite
  8. customto remove NaBr
  9. customThe solvent was removed
  10. customthe crude product was recrystallized from iPrOH

Quellen und Nachweise

ORD-Eintrag
ord-b077c7137be2452aa807d88173002700
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09206211B2

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