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

HRID 541336Notes

Reaction equation

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

Participants

Conditions

Temperature: 110 °C

Procedure

To a round-bottom flask was added a solution of methyl 2-ethyl-4-methylbenzoate (compound 48.1, 12.5 g, 70.1 mmol, 1.00 equiv) in AcOH (100 mL). NaIO4 (7.51 g, 35.1 mmol, 0.50 equiv) and I2 (21.4 g, 84.3 mmol, 1.20 equiv) were added in portions at 25° C. Sulfuric acid (1.60 g, 16.3 mmol, 0.20 equiv) was then added to the reaction mixture dropwise at 25° C. The resulting solution was stirred for 12 h at 110° C. in an oil bath, and then cooled to ambient temperature. The reaction was quenched with 150 mL of Na2S2O3 (aq., sat.). The aqueous phase was extracted with 2×200 mL of ethyl acetate. The combined organic layers were washed with 3×300 mL of sodium bicarbonate (aq.) and 1×150 mL of brine. The mixture was dried over anhydrous sodium sulfate and concentrated in vacuo. This resulted in 20.0 g (94%) of methyl 2-ethyl-5-iodo-4-methylbenzoate as a yellow oil.

Workup

temperaturecooled to ambient temperature
customThe reaction was quenched with 150 mL of Na2S2O3 (aq., sat.)
extractionThe aqueous phase was extracted with 2×200 mL of ethyl acetate
washThe combined organic layers were washed with 3×300 mL of sodium bicarbonate (aq.) and 1×150 mL of brine
dry with materialThe mixture was dried over anhydrous sodium sulfate
concentrationconcentrated in vacuo
customThis resulted in 20.0 g (94%) of methyl 2-ethyl-5-iodo-4-methylbenzoate as a yellow oil

Sources & evidence

ORD record: ord-3aaccffadd9844638b62eb15574f7f72
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871790B2

Reaction notes

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