Acetic Acid → 4-Butoxy-2,3-difluorophenol

HRID 1511485Notes

Reaction equation

HRID 1511485 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9](B(O)O)=[C:8]([F:15])[C:7]=1[F:16])[CH2:2][CH2:3][CH3:4].C(O)(=[O:19])C.OO.S([O-])(O)=O.[Na+]>C(OCC)(=O)C>[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([OH:19])=[C:8]([F:15])[C:7]=1[F:16])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 23665763Sodium BisulfiteHCID 54132493(4-Butoxy-2,3-difluorophenyl)boronic acid

Product 1

HCID 191034334-Butoxy-2,3-difluorophenol

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The compound (23) (40.0 g) and acetic acid (100 ml) were put in a reaction vessel under a nitrogen atmosphere, and hydrogen peroxide (31% aqueous solution; 40.4 ml) was added dropwise in the temperature range of 25° C. to 30° C., and the stirring was continued for another 2 hours. Then the reaction mixture was poured into a vessel containing sodium hydrogen sulfite solution (100 ml) and ethyl acetate (300 ml), and mixed. Then the mixture was allowed to separate into organic and aqueous phases, and the extraction was carried out. The organic phase obtained was washed sequentially with water and brine, and dried over anhydrous magnesium sulfate. Then the solvent was distilled off under reduced pressure, giving 31.7 g of 4-butoxy-2,3-difluorophenol (24). The yield based on the compound (23) was 90.2%.

Workup

  1. additionThen the reaction mixture was poured into a vessel
  2. additionmixed
  3. customto separate into organic and aqueous phases
  4. extractionthe extraction
  5. customThe organic phase obtained
  6. washwas washed sequentially with water and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThen the solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-6c772cb177ab4d6f9679198d892ca216
Source dataset
uspto-grants-2012_07
Patent number
US08216489B2

Reaction notes

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