Hydrochloric Acid → 7-Fluoro-4-hydroxy-2H-1-benzopyran-2-one

HRID 2116659Notes

Reaction equation

HRID 2116659 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[C:4]([OH:11])[CH:3]=1.[H-].[Na+].[CH2:14]([O:16]C(=O)OCC)C.Cl>C1(C)C=CC=CC=1.CCOC(C)=O>[F:1][C:2]1[CH:3]=[C:4]2[C:5]([C:8]([OH:10])=[CH:9][C:14](=[O:16])[O:11]2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7766Diethyl CarbonateHCID 24758Sodium hydrideHCID 27373264'-Fluoro-2'-hydroxyacetophenone

Product 1

HCID 546945707-Fluoro-4-hydroxy-2H-1-benzopyran-2-one

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
115 °C

Procedure

A solution of 1-(4-fluoro-2-hydroxyphenyl)ethanone (50 g, 0.33 mol) in toluene was added over 30 min to a suspension of NaH (60% oil, 65 g, 1.63 mol) in toluene. Then diethylcarbonate (59 mL, 0.49 mol) was added over 15 min and the reaction mixture was stirred at 115° C. for 6 h. The mixture was cooled to rt followed by the addition of HCl 2N and diluted with EtOAc. The organic phase was washed with brine, dried over Na2SO4 and evaporated. The residue was purified by trituration in hexane and Et2O to give the title compound.

Workup

  1. temperatureThe mixture was cooled to rt
  2. washThe organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. customThe residue was purified by trituration in hexane

Sources & evidence

ORD record
ord-0ee66c0372a048e291488d8e40fe0fca
Source dataset
uspto-grants-2008_10
Patent number
US07439260B2

Reaction notes

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