Methanol → 5-Chloro-2-fluoro-1-methoxy-3-(methylsulfinyl)benzene

HRID 591454Notes

Reaction equation

HRID 591454 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:11][CH3:12])[C:5]([F:10])=[C:6]([O:8][CH3:9])[CH:7]=1.C[OH:14]>O>[Cl:1][C:2]1[CH:3]=[C:4]([S:11]([CH3:12])=[O:14])[C:5]([F:10])=[C:6]([O:8][CH3:9])[CH:7]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 89767597(5-Chloro-2-fluoro-3-methoxyphenyl)(methyl)sulfane

Product 1

HCID 897678805-Chloro-2-fluoro-1-methoxy-3-(methylsulfinyl)benzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 5-chloro-2-fluoro-1-methoxy-3-(methylsulfanyl)benzene (576.1 mg), MeOH (20 mL) and water (4.0 mL) was added NaIO4 (894 mg) at 0° C. The mixture was stirred at room temperature for 1 day. The mixture was concentrated. The residue 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, and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (501 mg).

Workup

  1. concentrationThe mixture was concentrated
  2. additionThe residue was diluted with water
  3. filtrationThe precipitate was filtered off
  4. extractionthe filtrate was extracted with EtOAc
  5. washThe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-e323c59127c744a1ba29a0b3b023ced3
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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