Hydrogen Peroxide → 2,3-Difluoro-5-methylphenol

HRID 2260907Notes

Reaction equation

HRID 2260907 reaction equation
OO.[F:3][C:4]1[C:9]([F:10])=[CH:8][C:7]([CH3:11])=[CH:6][C:5]=1[O:12]B(O)O>S([O-])(O)=O.[Na+]>[F:3][C:4]1[C:9]([F:10])=[CH:8][C:7]([CH3:11])=[CH:6][C:5]=1[OH:12]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 231188412,3-Difluoro-5-methylphenylboric acid

Product 1

HCID 231188182,3-Difluoro-5-methylphenol

Reagents, catalysts & solvents 1

HCID 23665763Sodium BisulfiteSolvent

Procedure

Under cooling with an ice bath, 53.1 g of aqueous hydrogen peroxide was slowly added dropwise to the compound (3) having been dissolved in 300 mL, followed by stirring at room temperature for 3 hours. Under cooling with an ice bath, 100 mL of a saturated sodium hydrogensulfite aqueous solution was added dropwise thereto to terminate the reaction. The aqueous layer was extracted with diethyl ether, which was added to the organic layer, and the organic layer was washed with a saturated sodium hydrogensulfite aqueous solution and a saturated saline and then dried over anhydrous magnesium sulfate. The solvent was distilled off in vacuo to obtain 22.7 g of 2,3-difluoro-5-methylphenol (4).

Workup

  1. temperatureUnder cooling with an ice bath
  2. dissolutionhaving been dissolved in 300 mL
  3. temperatureUnder cooling with an ice bath
  4. customto terminate
  5. customthe reaction
  6. extractionThe aqueous layer was extracted with diethyl ether, which
  7. additionwas added to the organic layer
  8. washthe organic layer was washed with a saturated sodium hydrogensulfite aqueous solution
  9. dry with materiala saturated saline and then dried over anhydrous magnesium sulfate
  10. distillationThe solvent was distilled off in vacuo

Sources & evidence

ORD record
ord-4ecf643ab25c4906a12ec5cd57602a18
Source dataset
uspto-grants-2010_12
Patent number
US07846513B2

Reaction notes

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