Hydrogen Peroxide → 2-Fluoro-3-methoxyphenol

HRID 629476Notes

Reaction equation

HRID 629476 reaction equation
[F:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=1B(O)O.OO.S([O-])([O-])=[O:16].[Na+].[Na+]>C1COCC1>[F:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:16]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 24437Sodium SulfiteHCID 49857442-Fluoro-3-methoxyphenylboronic acid

Product 1

HCID 401517632-Fluoro-3-methoxyphenol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-fluoro-3-methoxyphenylboronic acid (30.4 g) in THF (300 mL) was added dropwise aqueous hydrogen peroxide (100 mL, 30% wt in water), and the mixture was heated with reflux for 1 hr. The reaction mixture was allowed to be cooled to room temperature, saturated aqueous sodium sulfite was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by combi flash (petroleum ether/ethyl acetate) to give the title compound (24.8 g).

Workup

  1. temperaturethe mixture was heated
  2. temperaturewith reflux for 1 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by combi flash (petroleum ether/ethyl acetate)

Sources & evidence

ORD record
ord-129600cd3804452d978af33be6c324a9
Source dataset
uspto-grants-2016_04
Patent number
US09315458B2

Reaction notes

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