Acetic Acid → 1-(2-Fluoro-3-hydroxyphenyl)ethanone

HRID 19160Notes

Reaction equation

HRID 19160 reaction equation
[C:1]([C:4]1[C:5]([F:13])=[C:6](B(O)O)[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2].C(O)(=[O:16])C.OO>O1CCCC1>[F:13][C:5]1[C:6]([OH:16])=[CH:7][CH:8]=[CH:9][C:4]=1[C:1](=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 16217905(3-Acetyl-2-fluorophenyl)boronic acid

Product 1

HCID 668947801-(2-Fluoro-3-hydroxyphenyl)ethanoneYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (3-acetyl-2-fluorophenyl)boronic acid (10.0 g, 0.055 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 5 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 1-(2-fluoro-3-hydroxy-phenyl)-ethanone (8.50 g, 100%) as a white 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-24a4464aef7f4202ae29151c30171f4a
Source dataset
uspto-grants-2010_06
Patent number
US07741327B2

Reaction notes

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