Phenol → 5-Phenoxy-2-benzofuran-1(3H)-one

HRID 516984Notes

Reaction equation

HRID 516984 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(CC(=O)C)(=O)C.Br[C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[C:21](=[O:22])[O:20][CH2:19]2.C(=O)([O-])[O-].[K+].[K+]>[Cu](Br)Br.O.CN(C=O)C>[O:7]([C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[C:21](=[O:22])[O:20][CH2:19]2)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 996PhenolHCID 11430Potassium CarbonateHCID 31261AcetylacetoneHCID 6031445-Bromophthalide

Product 1

HCID 445585805-Phenoxy-2-benzofuran-1(3H)-oneYield 72%

Reagents, catalysts & solvents 3

HCID 24611Copper bromide (CuBr2)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A reactor was charged with DMF (68 Kg), and stirring was initiated. The reactor was then charged with phenol (51 Kg), acetylacetone (8 Kg), 5-bromophthalide (85 Kg), copper bromide (9 Kg), and potassium carbonate (77 Kg). The mixture was heated above 85° C. and maintained until reaction completion and then cooled. Water was added. Solid was filtered and washed with water. Solid was dissolved in dichloromethane, and washed with aqueous HCl and then with water. Solvent was removed under pressure and methanol was added. The mixture was stirred and filtered. Solid was washed with methanol and dried in an oven giving 5-phenoxyphthalide (Yield: 72%, HPLC: 99.6%).

Workup

  1. temperatureThe mixture was heated above 85° C.
  2. temperaturemaintained until reaction completion
  3. temperaturecooled
  4. filtrationSolid was filtered
  5. washwashed with water
  6. dissolutionSolid was dissolved in dichloromethane
  7. washwashed with aqueous HCl
  8. customSolvent was removed under pressure and methanol
  9. additionwas added
  10. stirringThe mixture was stirred
  11. filtrationfiltered
  12. washSolid was washed with methanol
  13. customdried in an oven

Sources & evidence

ORD record
ord-c452ca595a0c4e9a8cfe19d262b8cda9
Source dataset
uspto-grants-2015_08
Patent number
US09115085B2

Reaction notes

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