Hydrogen Peroxide → 2,3-Difluorophenol

HRID 2292426Notes

Reaction equation

HRID 2292426 reaction equation
[OH:1]O.[F:3][C:4]1[C:9]([F:10])=[CH:8][CH:7]=[CH:6][C:5]=1B(O)O>C(OCC)C>[F:3][C:4]1[C:9]([F:10])=[CH:8][CH:7]=[CH:6][C:5]=1[OH:1]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 2734333(2,3-Difluorophenyl)boronic acid

Product 1

HCID 808792,3-Difluorophenol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Hydrogen peroxide (10%, 340 cm3, 1 mol) was added dropwise to a stirred solution of compound from Example 36 (47 g, 0.3 mol) in diethyl ether (350 cm3) heated under reflux. The stirred mixture was heated under reflux for a further 2.5 h then cooled. The ethereal layer was separated and the aqueous layer extracted with diethyl ether (2×200 cm3). The combined ethereal layers were washed with sodium hydroxide (10%, 4×100 cm3) and the separated aqueous layers acidified with 36% hydrochloric acid. The product was extracted into diethyl ether (3×100 cm3), and the combined ethereal extracts washed with water and dried (MgSO4). The solvent was removed in vacuo to give an off white solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. temperatureThe stirred mixture was heated
  4. temperatureunder reflux for a further 2.5 h
  5. temperaturethen cooled
  6. customThe ethereal layer was separated
  7. extractionthe aqueous layer extracted with diethyl ether (2×200 cm3)
  8. washThe combined ethereal layers were washed with sodium hydroxide (10%, 4×100 cm3)
  9. extractionThe product was extracted into diethyl ether (3×100 cm3)
  10. washthe combined ethereal extracts washed with water
  11. dry with materialdried (MgSO4)
  12. customThe solvent was removed in vacuo
  13. customto give an off white solid

Sources & evidence

ORD record
ord-79ae9ba3597a47858b7d273a596cbe1f
Source dataset
uspto-grants-1997_11
Patent number
US05683623

Reaction notes

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