Acetic Acid → 2,6-Difluoro-3-methoxyphenol

HRID 19121Notes

Reaction equation

HRID 19121 reaction equation
[F:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[C:4]([F:10])[C:3]=1B(O)O.C(O)(=[O:16])C.OO>O1CCCC1>[F:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[C:4]([F:10])[C:3]=1[OH:16]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 27831312,6-Difluoro-3-methoxybenzeneboronic acid

Product 1

HCID 36828622,6-Difluoro-3-methoxyphenolYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,6-difluoro-3-methoxy-phenylboronic acid (10.0 g, 0.053 mol) in tetrahydrofuran (160 mL) was added glacial acetic acid (60 mL). The resulting mixture was cooled to 0° C. before hydrogen peroxide (50% aqueous solution, 8 mL) was added. The resulting mixture was allowed to come to room temperature and stirred for 120 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 2,6-difluoro-3-methoxy-phenol (7.50 g, 88%) as a pale brown solid.

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-e127866cdd7a4ef6a9febf1bd21ca98f
Source dataset
uspto-grants-2010_06
Patent number
US07741327B2

Reaction notes

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