Methanol → 2-Fluoro-1-methoxy-5-methyl-3-(methylsulfinyl)benzene

HRID 591442Notes

Reaction equation

HRID 591442 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

HCID 887MethanolHCID 89767603(2-Fluoro-3-methoxy-5-methylphenyl)(methyl)sulfane

Product 1

HCID 897676932-Fluoro-1-methoxy-5-methyl-3-(methylsulfinyl)benzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

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

  1. filtrationThe precipitate was filtered off
  2. extractionthe filtrate was extracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. 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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