Methanol → Methyl 2-iodo-5-(methylsulfonyl)benzoate

HRID 2374237Notes

Reaction equation

[I:1][C:2]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH:15]1N=CN(C(N2C=NC=C2)=O)C=1.CO>C1COCC1>[CH3:15][O:5][C:4](=[O:6])[C:3]1[CH:7]=[C:8]([S:11]([CH3:14])(=[O:13])=[O:12])[CH:9]=[CH:10][C:2]=1[I:1]

Participants

Conditions

Temperature: 70 °C

Procedure

To 2-Iodo-5-methanesulfonyl-benzoic acid (Example C, 10.0 g, 30.7 mmolin 250 ml THF was added CDI (5.50 g, 33.7 mmol) and the mixture heated at 70° C. for 1 h. Methanol (12.4 ml, 307 mmol) was then added and the mixture was heated at 70° C. for a further 1 h. The mixture was then cooled to room temperature and concentrated in vacuo. The residue was chromatographed over SiO2 (ethyl acetate/dichloromethane 4:1) to afford the title compound (8.95 g, 86%) as white crystalline solid.

Workup

temperaturethe mixture was heated at 70° C. for a further 1 h
temperatureThe mixture was then cooled to room temperature
concentrationconcentrated in vacuo
customThe residue was chromatographed over SiO2 (ethyl acetate/dichloromethane 4:1)

Sources & evidence

ORD record: ord-6d72f052e5664629a83f2deadbc34c82
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07462617B2

Reaction notes

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