Methanol → 2,6-Dinitrophenyl methyl ether

HRID 1501875Notes

Reaction equation

HRID 1501875 reaction equation
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]

Participants

3

Reactant 2

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

Product 1

HCID 5977192,6-Dinitrophenyl methyl ether

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-b077c7137be2452aa807d88173002700
Source dataset
uspto-grants-2015_12
Patent number
US09206211B2

Reaction notes

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