Acetic Acid → 3-Ethoxy-2,6-difluorophenol

HRID 19115Notes

Reaction equation

HRID 19115 reaction equation
[CH2:1]([O:3][C:4]1[C:5]([F:14])=[C:6](B(O)O)[C:7]([F:10])=[CH:8][CH:9]=1)[CH3:2].C(O)(=[O:17])C.OO>O1CCCC1>[CH2:1]([O:3][C:4]1[C:5]([F:14])=[C:6]([OH:17])[C:7]([F:10])=[CH:8][CH:9]=1)[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 162178932,6-Difluoro-3-ethoxyphenylboronic acid

Product 1

HCID 552757683-Ethoxy-2,6-difluorophenolYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-ethoxy-2,6-difluoro-phenylboronic acid (5.0 g, 0.025 mol) in tetrahydrofuran (80 mL) was added glacial acetic acid (30 mL). The resulting mixture was cooled to 0° C. before hydrogen peroxide (50% aqueous solution, 4 mL) was added. The resulting mixture was allowed to come to room temperature and stirred for 65 h. The mixture was evaporated and the residue was dissolved in ethyl acetate, washed with hydrochloric acid (0.5N), water and brine. The organic phase was dried, filtered and evaporated which afforded 3-ethoxy-2,6-difluoro-phenol (4.25 g, 99%) as a brown oil.

Workup

  1. additionwas added
  2. customto come to room temperature
  3. customThe mixture was evaporated
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washwashed with hydrochloric acid (0.5N), water and brine
  6. customThe organic phase was dried
  7. filtrationfiltered
  8. customevaporated which

Sources & evidence

ORD record
ord-7a5eea20e25641bcabd0ad9c71356794
Source dataset
uspto-grants-2010_06
Patent number
US07741327B2

Reaction notes

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