Iodine → 4-Chloro-5-iodo-2-methylbenzoic acid

HRID 541294Notes

Reaction equation

HRID 541294 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([CH3:11])[CH:3]=1.[I:12]I.S(=O)(=O)(O)O>C(O)(=O)C>[Cl:1][C:2]1[C:10]([I:12])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([CH3:11])[CH:3]=1

Participants

5

Reactant 3

HCID 807IodineHCID 1118Sulfuric AcidHCID 3482694-Chloro-2-methylbenzoic acid

Product 1

HCID 682889484-Chloro-5-iodo-2-methylbenzoic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
110 °C

Procedure

To a round-bottom flask was added a solution of 4-chloro-2-methylbenzoic acid (30.0 g, 176 mmol, 1.00 equiv) in acetic acid (300 mL). NaIO4 (19.0 g, 88.8 mmol, 0.50 equiv), I2 (49.0 g, 193 mmol, 1.10 equiv), and sulfuric acid (3 mL) were added to the reaction. The resulting mixture was stirred overnight at 110° C. After cooling to ambient temperature, the reaction was carefully quenched with 500 mL of Na2S2O3 (aq., sat.). The resulting solids were collected by filtration and then dissolved in 500 mL of ethyl acetate. The organic phase was washed with 2×200 mL of brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. This resulted in 20.0 g (38%) of 4-chloro-5-iodo-2-methylbenzoic acid as a white solid.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. customthe reaction was carefully quenched with 500 mL of Na2S2O3 (aq., sat.)
  3. filtrationThe resulting solids were collected by filtration
  4. dissolutiondissolved in 500 mL of ethyl acetate
  5. washThe organic phase was washed with 2×200 mL of brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThis resulted in 20.0 g (38%) of 4-chloro-5-iodo-2-methylbenzoic acid as a white solid

Sources & evidence

ORD record
ord-6accd657c61143f78d8345e0113e9818
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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