Methanol → 2-Fluoro-1-methoxy-5-methyl-3-(methylsulfinyl)benzene
Reaction equation
[F:1][C:2]1[C:7]([S:8][CH3:9])=[CH:6][C:5]([CH3:10])=[CH:4][C:3]=1[O:11][CH3:12].C[OH:14]>O>[F:1][C:2]1[C:7]([S:8]([CH3:9])=[O:14])=[CH:6][C:5]([CH3:10])=[CH:4][C:3]=1[O:11][CH3:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a mixture of 2-fluoro-1-methoxy-5-methyl-3-(methylsulfanyl)benzene (557.4 mg), MeOH (20 mL) and water (4 mL) was added NaIO4 (960 mg) at 0° C. The mixture was stirred at room temperature over weekend. The mixture was diluted with water. The precipitate was filtered off, and the filtrate was extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (486 mg).
Workup
- filtrationThe precipitate was filtered off
- extractionthe filtrate was extracted with EtOAc
- washThe organic layer was washed with brine
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was purified by silica gel column chromatography (EtOAc/hexane)
Sources & evidence
- ORD record
- ord-5925f71deda44fc398619b779216804f
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09238639B2
Reaction notes
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