Nitric Acid → methyl 2-bromo-3,5-dinitrobenzoate

HRID 1064096Notes

Reaction equation

HRID 1064096 reaction equation
S(=O)(=O)(O)O.[CH3:6][O:7][C:8](=[O:19])[C:9]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:10]=1[Br:18].[N+:20]([O-])([OH:22])=[O:21]>C(OCC)(=O)C>[CH3:6][O:7][C:8](=[O:19])[C:9]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[C:11]([N+:20]([O-:22])=[O:21])[C:10]=1[Br:18]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 245494Methyl 2-Bromo-5-nitrobenzoate

Product 1

HCID 293192methyl 2-bromo-3,5-dinitrobenzoateYield 65%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

Concentrated sulfuric acid (20 mL) was slowly added to 2-bromo-5-nitro-benzoic acid methyl ester (20.52 g, 78.91 mmol) with stirring. After a few minutes, fuming nitric acid (20 mL) was added and the mixture was capped and heated at 40° C. for approximately 60 hours at which point the flask was cooled to ambient temperature, carefully opened, and the reaction was poured onto ice water and ethyl acetate. The product was extracted into ethyl acetate and washed twice with H2O, twice with saturated aqueous NaHCO3, brine, dried (Na2SO4), and filtered to afford Intermediate 6(a) (15.64 g, 51.26 mmol) as a cream solid in 65% yield.

Workup

  1. waitAfter a few minutes
  2. customthe mixture was capped
  3. temperaturewas cooled to ambient temperature
  4. extractionThe product was extracted into ethyl acetate
  5. washwashed twice with H2O, twice with saturated aqueous NaHCO3, brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered

Sources & evidence

ORD record
ord-5b816330c24e4745885ac0b58f6205ae
Source dataset
uspto-grants-2005_11
Patent number
US06967198B2

Reaction notes

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