Iodine → Methyl 4-(cyclobutylmethyl)-5-iodo-2-methylbenzoate

HRID 541306Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

To a round-bottom flask was added a solution of methyl 4-(cyclobutylmethyl)-2-methylbenzoate (compound 189.1, 8.40 g, 38.5 mmol, 1.00 equiv) in AcOH (150 mL). NaIO4 (5.00 g, 23.4 mmol, 0.50 equiv), iodine (10.0 g, 39.4 mmol, 1.00 equiv), and sulfuric acid (0.3 mL) were added to the reaction mixture. The resulting solution was stirred at 60° C. for 12 h. After cooling to room temperature, the reaction was quenched with 200 mL of NaHSO3 (aq). The mixture was extracted with 2×200 mL of ethyl acetate, and the combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified using silica gel column chromatography with ethyl acetate/petroleum ether (20:1) as eluent to furnish 8.00 g (60%) of methyl 4-(cyclobutylmethyl)-5-iodo-2-methylbenzoate as a white solid.

Workup

temperatureAfter cooling to room temperature
customthe reaction was quenched with 200 mL of NaHSO3 (aq)
extractionThe mixture was extracted with 2×200 mL of ethyl acetate
dry with materialthe combined organic layers were dried over anhydrous sodium sulfate
concentrationconcentrated in vacuo
customThe residue was purified

Sources & evidence

ORD record: ord-693e0f6a088c4fef8909d68ac12ccfba
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871790B2

Reaction notes

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