Sodium Methoxide → 1-Bromo-2-methoxy-4-(methylsulfonyl)benzene

HRID 1846008Notes

Reaction equation

HRID 1846008 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:4][C:3]=1F.[CH3:13][O-:14].[Na+]>CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:4][C:3]=1[O:14][CH3:13]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 467389084-Bromo-3-fluorophenyl methyl sulphone

Product 1

HCID 672165191-Bromo-2-methoxy-4-(methylsulfonyl)benzeneYield 53%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-bromo-2-fluoro-4-(methylsulfonyl)benzene (Preparation 14, 1.5 g, 5.93 mmol) in MeOH (12 mL) was added sodium methoxide (480 mg, 8.89 mmol) and the reaction mixture was irradiated at 100° C. in the microwave for 1.5 hours. After this time the reaction was quenched with water (50 mL) and the product was extract with EtOAc (3×50 mL). The combined organic layers were dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography eluting with 20-40% EtOAc in heptane to afford the title compound as colourless solid in 53% yield.

Workup

  1. customthe reaction mixture was irradiated at 100° C. in the microwave for 1.5 hours
  2. customAfter this time the reaction was quenched with water (50 mL)
  3. extractionthe product was extract with EtOAc (3×50 mL)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography
  8. washeluting with 20-40% EtOAc in heptane

Sources & evidence

ORD record
ord-6479e957b5b74f21994d07a6232790e5
Source dataset
uspto-grants-2015_02
Patent number
US08952008B2

Reaction notes

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