Nitric Acid → Methyl 4-iodo-3-nitrobenzoate

HRID 400602Notes

Reaction equation

HRID 400602 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([I:10])=[CH:6][CH:5]=1.[N+:12]([O-])([OH:14])=[O:13].C(OCC)(=O)C>S(=O)(=O)(O)O>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([I:10])=[C:6]([N+:12]([O-:14])=[O:13])[CH:5]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 8857Ethyl AcetateHCID 69273Methyl 4-iodobenzoate

Product 1

HCID 297884Methyl 4-iodo-3-nitrobenzoateYield 33%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
40 °C

Procedure

A solution of 4-iodobenzoic acid methyl ester (5.24 g, 20.0 mmol) in sulfuric acid was treated with 1.43 mL of concentrated nitric acid in a dropwise fashion at 0° C. After 5 hours at room temperature, the reaction mixture was heated to 40° C. for 1 hour. The resulting orange solution was added to 100 g of ice, treated with 200 mL of ethyl acetate, shaken for 30 minutes, and filtered. The phases were separated and the aqueous layer was extracted with 200 mL of ethyl acetate. The combined organic layers were washed with saturated sodium bicarbonate solution and brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was passed through a column of silica gel (100% ethyl acetate) to give 2.0 g of 4-iodo-3-nitrobenzoic acid methyl ester as a yellow solid (33% yield).

Workup

  1. filtrationfiltered
  2. customThe phases were separated
  3. extractionthe aqueous layer was extracted with 200 mL of ethyl acetate
  4. washThe combined organic layers were washed with saturated sodium bicarbonate solution and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5267acd999f1492985e32be1a7da8c87
Source dataset
uspto-grants-2014_06
Patent number
US08741897B2

Reaction notes

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