Iodine → Methyl 4-cyclopropyl-2-ethyl-5-iodobenzoate

HRID 541369Notes

Reaction equation

HRID 541369 reaction equation
[CH:1]1([C:4]2[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([CH2:14][CH3:15])[CH:5]=2)[CH2:3][CH2:2]1.[I:16]I.S(=O)(=O)(O)O>CC(O)=O>[CH:1]1([C:4]2[C:13]([I:16])=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([CH2:14][CH3:15])[CH:5]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 807IodineHCID 1118Sulfuric AcidHCID 68288825Methyl 4-cyclopropyl-2-ethylbenzoate2×

Product 1

HCID 68288857Methyl 4-cyclopropyl-2-ethyl-5-iodobenzoateYield 49.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

To a round-bottom flask was added a solution of methyl 4-cyclopropyl-2-ethylbenzoate (compound 226.3, 5.00 g, 24.5 mmol, 1.00 equiv) in AcOH (40 mL). I2 (6.80 g, 26.8 mmol, 1.10 equiv), NaIO4 (2.60 g, 12.2 mmol, 0.50 equiv), and sulfuric acid (400 mg, 4.08 mmol, 0.15 equiv) were added to the reaction. The resulting solution was stirred for 2 h at 50° C. After cooling to ambient temperature, the reaction was carefully quenched with Na2S2O3 (aq., sat.). The mixture was extracted with 2×100 mL of ethyl acetate, and the combined organic layers were dried over sodium sulfate and concentrated in vacuo. The residue was purified using silica gel column chromatography with petroleum ether/ethyl acetate (20:1) as eluent to furnish 4.00 g (49%) of methyl 4-cyclopropyl-2-ethyl-5-iodobenzoate as a yellow oil.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. customthe reaction was carefully quenched with Na2S2O3 (aq., sat.)
  3. extractionThe mixture was extracted with 2×100 mL of ethyl acetate
  4. dry with materialthe combined organic layers were dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified

Sources & evidence

ORD record
ord-3f532688706c45dda5eddea1fd31253f
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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