Iodine → 3-Iodo-5-nitrobenzoic acid

HRID 1013262Notes

Reaction equation

HRID 1013262 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=[O:8])([O-:3])=[O:2].[I:13]I>OS(O)(=O)=O>[I:13][C:11]1[CH:10]=[C:6]([CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=1)[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 807IodineHCID 84973-Nitrobenzoic acid

Product 1

HCID 805803-Iodo-5-nitrobenzoic acidYield 67.7%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
85 °C

Procedure

To a mixture of 3-Nitro-benzoic acid (114 g, 0.68 mol) and I2 (138.2 g) was added dropwise H2SO4 (conc., 230 mL). The reaction mixture was stirred at 85° C. for 18 hours, then was cooled and poured onto ice. The resulting mixture was partitioned between EtOAc and saturated aqueous NaHSO3. The combined organic layers were washed with water, dried over Na2SO4, filtered and concentrated under reduced pressure to give 108 g of 3-iodo-5-nitro-benzoic acid as a pale yellow solid, MS (M+H)=294.

Workup

  1. temperaturewas cooled
  2. additionpoured onto ice
  3. customThe resulting mixture was partitioned between EtOAc and saturated aqueous NaHSO3
  4. washThe combined organic layers were washed with water
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6b029b1b4a5247b39fc5720ed6ba8b82
Source dataset
uspto-grants-2011_07
Patent number
US07981914B2

Reaction notes

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