Nitric Acid → 1-Bromo-4-methoxy-2,3-dinitrobenzene

HRID 1661888Notes

Reaction equation

HRID 1661888 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[N+:13]([O-])([OH:15])=[O:14].S(=O)(=O)(O)O>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([N+:13]([O-:15])=[O:14])[C:3]=1[N+:10]([O-:12])=[O:11]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 792884-Bromo-3-nitroanisole

Product 1

HCID 577720761-Bromo-4-methoxy-2,3-dinitrobenzene

Procedure

1.0 g (4.3 mmol) 4-bromo-3-nitroanisole is nitrated by dropwise addition of 1.0 ml of a mixture of 0.4 ml nitric acid (100%) and 0.6 ml concentrated sulfuric acid. Stirring is continued for 1 h. After that the reaction mixture is poured on water and extracted (3×) with ethyl acetate. The combined organic layers are washed with water and brine (2×), dried over MgSO4, filtered and concentrated in vacuo. The residue is purified by flash-chromatography on silica gel (hexane:EtOAc=1:1) to afford 630 mg of the title compound as yellow crystals.

Workup

  1. additionAfter that the reaction mixture is poured on water
  2. extractionextracted (3×) with ethyl acetate
  3. washThe combined organic layers are washed with water and brine (2×)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by flash-chromatography on silica gel (hexane:EtOAc=1:1)

Sources & evidence

ORD record
ord-a981a240857d49e1aa913b7a9b993940
Source dataset
uspto-grants-2011_10
Patent number
US08030497B2

Reaction notes

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