Acetic Acid → HCID 66894508, compound

HRID 19110

Reaction equation

HRID 19110 reaction equation
[CH2:1]([O:3][C:4]1[C:5]([F:13])=[C:6](B(O)O)[CH:7]=[CH:8][CH:9]=1)[CH3:2].C(O)(=[O:16])C.OO>O1CCCC1>[CH2:1]([O:3][C:4]1[C:5]([F:13])=[C:6]([OH:16])[CH:7]=[CH:8][CH:9]=1)[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 162177593-Ethoxy-2-fluorophenylboronic Acid (contains varying amounts of Anhydride)

Product 1

HCID 66894508HCID 66894508, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-ethoxy-2-fluoro-phenylboronic acid (10.0 g, 0.054 mol) in tetrahydrofuran (150 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 23 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 to give 3-ethoxy-2-fluoro-phenol (6.00 g, 71%) 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

Sources & evidence

ORD record
ord-7adf2dfca726471ca42cb65a1100631d
Source dataset
uspto-grants-2010_06
Patent number
US07741327B2

Linked notes

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