Reacción #58871

ord-64e03f43ee504125a8fbde98ebe10950

Ecuación de reacción

Oc1cc(Br)ccc1F
2-fluoro-5-bromophenol
O=C([O-])[O-].[K+].[K+]
potassium carbonate
[I-].[Na+]
sodium iodide
FC(F)=CCCBr
4-bromo-1,1-difluoro-1-butene
FC(F)=CCCOc1cc(Br)ccc1F
4-bromo-2-(4,4-difluorobut-3-enyloxy)-1-fluorobenzene
Rendimiento 63.0%

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otrowas placed in a pressure vessel
  2. 2
    Temperaturaheated in a 82° oil bath for 15 hours
  3. 3
    TemperaturaThe reaction mixture was cooled
  4. 4
    Filtraciónfiltered
  5. 5
    Otroevaporated in vacuo
  6. 6
    OtroThe resultant residue was purified by flash chromatography (silica gel, eluant

Procedimiento

A mixture of 2-fluoro-5-bromophenol (2.40 g), potassium carbonate (2.31 m), Aliquat 336 (5 drops), sodium iodide (catalytic) and 4-bromo-1,1-difluoro-1-butene (1.79 mL) in methyl ethyl ketone was placed in a pressure vessel and heated in a 82° oil bath for 15 hours. The reaction mixture was cooled, diluted with dichloromethane, filtered and evaporated in vacuo. The resultant residue was purified by flash chromatography (silica gel, eluant: 2.5% ethyl acetate/hexane to afford 4-bromo-2-(4,4-difluorobut-3-enyloxy)-1-fluorobenzene, 2.23 g (63% yield), identified by NMR analysis.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07423158B2uspto-grants-2008_09