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

HRID 541299Notes

Reaction equation

HRID 541299 reaction equation
[CH:1]1([C:5]2[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([CH2:15][CH3:16])[CH:6]=2)[CH2:4][CH2:3][CH2:2]1.[I:17]I.S(=O)(=O)(O)O>C(O)(=O)C>[CH:1]1([C:5]2[C:14]([I:17])=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([CH2:15][CH3:16])[CH:6]=2)[CH2:2][CH2:3][CH2:4]1

Participants

5

Reactant 3

HCID 807IodineHCID 1118Sulfuric AcidHCID 68288811Methyl 4-cyclobutyl-2-ethylbenzoate2×

Product 1

HCID 68288985Methyl 4-cyclobutyl-2-ethyl-5-iodobenzoateYield 86.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methyl 4-cyclobutyl-2-ethylbenzoate (compound 181.3, 7.70 g, 35.3 mmol, 1.00 equiv) in acetic acid (80 mL) was added iodine (8.98 g, 35.4 mmol, 1.00 equiv), NaIO4 (3.78 g, 17.7 mmol, 0.50 equiv), and sulfuric acid (0.870 g, 8.87 mmol, 0.25 equiv). The reaction mixture was stirred at 60° C. overnight. After cooling to room temperature, the reaction was slowly quenched with Na2S2O3 (aq., sat.). The mixture was extracted with 200 mL of ethyl acetate and the organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (1:50) to furnish 10.5 g (86%) of the desired product as a colorless solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe reaction was slowly quenched with Na2S2O3 (aq., sat.)
  3. extractionThe mixture was extracted with 200 mL of ethyl acetate
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (1:50)

Sources & evidence

ORD record
ord-8c7edd3541034dcdbc1aa29991871df0
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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