Sulfuric Acid → Methyl 4-bromo-3-nitrobenzoate

HRID 2197968Notes

Reaction equation

HRID 2197968 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].S(=O)(=O)(O)O.[C:19](OCC)(=O)C.O>CO.S(=O)(=O)(O)O>[CH3:19][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([Br:1])=[C:3]([N+:11]([O-:13])=[O:12])[CH:4]=1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 2329864-Bromo-3-nitrobenzoic acidHCID 22728543Water ethylacetate

Product 1

HCID 2736829Methyl 4-bromo-3-nitrobenzoate

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 887MethanolSolvent2×

Conditions

Temperature
90 °C

Procedure

Commercially available 4-bromo-3-nitro-benzoic acid (1.17 g, 4.76 mmol) was dissolved in methanol (5 mL) containing five drops of concentrated sulfuric acid. The mixture was heated in air at 90° C. for six hours and more MeOH (7 mL) followed by concentrated sulfuric acid (0.6 mL) was added. Heating was continued another 24 hours. Extractive work up (ethyl acetate-water) followed by drying over MgSO4, filtered and concentrated under vacuum giving the title compound in quantitative yield.

Workup

  1. additionwas added
  2. temperatureHeating
  3. dry with materialby drying over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-99bbbe5f8eb44a329162cd8f5efe9ee8
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

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