Water → Methyl 4-iodo-3-nitrobenzoate

HRID 2044210Notes

Reaction equation

HRID 2044210 reaction equation
[I: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]([O-])(O)=O.[Na+].O>CO>[CH3:19][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([I:1])=[C:3]([N+:11]([O-:13])=[O:12])[CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 112085984-Iodo-3-nitrobenzoic acid

Product 1

HCID 297884Methyl 4-iodo-3-nitrobenzoateYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-iodo-3-nitrobenzoic acid (3 g, 10 mmol) in methanol (30 ml) cooled to 0° C., sulfuric acid (3.4 g, 34.6 mmol) is added slowly. The reaction mixture is warmed to room temperature and then refluxed (˜70° C.) for 8 hours. After cooling, the reaction mixture is neutralized with solid NaHCO3 and the salts are filtered. The filtrate is evaporated under reduced pressure. To the residue obtained, water (30 ml) is added and the mixture extracted with MTBE (30 ml×2). The combined organic phase is washed with brine, dried using anhydrous sodium sulfate and filtered. After evaporating the solvent under reduced pressure, 4-iodo-3-nitro-benzoic acid methyl ester is obtained as a yellow solid (2.67 g, 85% yield, 98% HPLC).

Workup

  1. temperaturerefluxed (˜70° C.) for 8 hours
  2. temperatureAfter cooling
  3. filtrationthe salts are filtered
  4. customThe filtrate is evaporated under reduced pressure
  5. customTo the residue obtained
  6. extractionthe mixture extracted with MTBE (30 ml×2)
  7. washThe combined organic phase is washed with brine
  8. customdried
  9. filtrationfiltered
  10. customAfter evaporating the solvent under reduced pressure

Sources & evidence

ORD record
ord-0b59ff7c9476474b9ce0f34ddcaa6235
Source dataset
uspto-grants-2013_11
Patent number
US08586792B2

Reaction notes

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