Ethyl Acetate → 4-Methyl-3(2H)-benzofuranone

HRID 591047Notes

Reaction equation

HRID 591047 reaction equation
[F-].[K+].Br[CH2:4][C:5]([C:7]1[C:12]([CH3:13])=[CH:11][CH:10]=[CH:9][C:8]=1[OH:14])=[O:6].C(OCC)(=O)C>CN(C)C=O>[CH3:13][C:12]1[C:7]2[C:5](=[O:6])[CH2:4][O:14][C:8]=2[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 522689Potassium FluorideHCID 596067981154740-59-6

Product 1

HCID 5905344-Methyl-3(2H)-benzofuranoneYield 46.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium fluoride (0.85 g, 14.7 mmol) was added to a solution of 2-bromo-1-(2-hydroxy-6-methylphenyl)ethan-1-one (26b) (1.5 g, 6.5 mmol) in anhydrous dimethylformamide (25 mL). The reaction mixture was stirred at room temperature for 4 days. Ethyl acetate (75 mL) was added and the mixture was washed with brine (3×100 mL). The organic layer was dried over sodium sulfate and evaporated to dryness. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 95/5 to 80/20) to provide the desired benzofuran-3-one (26c) (450 mg, 3.04 mmol, 46%).

Workup

  1. washthe mixture was washed with brine (3×100 mL)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customevaporated to dryness
  4. customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 95/5 to 80/20)

Sources & evidence

ORD record
ord-6db6a9b94e1e488390b028005086fe23
Source dataset
uspto-grants-2016_01
Patent number
US09238026B2

Reaction notes

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