Reacción #43586

ord-ae2de73b0a5c4c679f9b21e0b468d267

Ecuación de reacción

O=Cc1cc(O)c(O)c(F)c1
3-fluoro-4,5-dihydroxybenzaldehyde
O=C([O-])[O-].[K+].[K+]
potassium carbonate
BrCCBr
1,2-dibromoethane
O=Cc1cc(F)c2c(c1)OCCO2
desired compound
Rendimiento 95.4%
O=Cc1cc(F)c2c(c1)OCCO2
8-fluoro-2,3-dihydro-1,4-benzodioxin-6-carboxaldehyde
Rendimiento 95.4%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otrowas removed under reduced pressure
  2. 2
    workup.ADDITIONThe reaction mixture was then treated with dichloromethane and water
  3. 3
    ExtracciónThe aqueous phase was extracted twice with dichloromethane
  4. 4
    Otrothe combined organic phases were dried
  5. 5
    Otrothe solvent was removed under reduced pressure

Procedimiento

To a solution of 3-fluoro-4,5-dihydroxybenzaldehyde (0.66 g, 4.2 mmol) in DMF (30 ml) was added potassium carbonate (1.15 g, 8.3 mmol) and 1,2-dibromoethane (0.72 ml, 8.3 mmol) and the resultant mixture was heated to 80° C. for 18 h before the solvent was removed under reduced pressure. The reaction mixture was then treated with dichloromethane and water. The aqueous phase was extracted twice with dichloromethane and the combined organic phases were dried and the solvent was removed under reduced pressure to give the desired compound as a cream solid (0.73 g, 95%).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07732461B2uspto-grants-2010_06