Iodine → Methyl 2-bromo-5-iodo-4-methylbenzoate

HRID 541308Notes

Reaction equation

HRID 541308 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[I:13]I.S(=O)(=O)(O)O>CC(O)=O>[Br:1][C:2]1[CH:11]=[C:10]([CH3:12])[C:9]([I:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 807IodineHCID 1118Sulfuric AcidHCID 21779704Methyl 2-bromo-4-methylbenzoate

Product 1

HCID 69844638Methyl 2-bromo-5-iodo-4-methylbenzoateYield 89.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a round-bottom flask was added a mixture of methyl 2-bromo-4-methylbenzoate (2.00 g, 7.86 mmol, 1.00 equiv) in AcOH (20 mL). I2 (2.45 g, 9.65 mmol, 1.10 equiv), NaIO4 (950 mg, 4.42 mmol, 0.50 equiv), and sulfuric acid (0.1 mL, 0.15 equiv) were added and the resulting mixture was stirred at 100° C. overnight. After cooling to ambient temperature, the reaction was carefully quenched with Na2S2O3 (aq., sat.). The resulting mixture was extracted with 2×50 mL of ethyl acetate. The combined organic layers were dried (Na2SO4) and concentrated in vacuo to yield 2.50 g (81%) of the title compound as an off-white solid.

Workup

  1. additionTo a round-bottom flask was added
  2. temperatureAfter cooling to ambient temperature
  3. customthe reaction was carefully quenched with Na2S2O3 (aq., sat.)
  4. extractionThe resulting mixture was extracted with 2×50 mL of ethyl acetate
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e045711f0c8648bfb6adecd963342007
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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