Reacción #81602

Ecuación de reacción

hydrogen

Sodium hydride

1,3,5-tribromobenzene

4-fluorophenol

→

title compound

Rendimiento 32.5%

1,3-Dibromo-5-(4-fluorophenoxy)benzene

Rendimiento 32.5%

Disolventes

collidine

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas heated
2. 2
   Temperaturaunder reflux
3. 3
   TemperaturaIt was then cooled
4. 4
   Filtraciónfiltered
5. 5
   LavadoThe residue was washed with ethyl acetate
6. 6
   Otrothe combined filtrate and washings were partitioned between ethyl acetate and water
7. 7
   LavadoThe organic layer was washed twice with brine
8. 8
   Otroevaporated
9. 9
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate
10. 10
    Filtraciónthe solution was filtered
11. 11
    Lavadowashed several times with citric acid solution
12. 12
    Secadodried (MgSO4)
13. 13
    OtroThe solvent was evaporated
14. 14
    workup.DISSOLUTIONthe residue was dissolved in hot hexane
15. 15
    FiltraciónThe solution was filtered
16. 16
    Otrothe filtrate was evaporated
17. 17
    OtroThe residue was chromatographed on silica

Procedimiento

Sodium hydride (3.24 g of 60% suspension in mineral oil was added portionwise to a stirred mixture of 1,3,5-tribromobenzene (76.4 g), 4-fluorophenol (18.16 g), and cuprous oxide (11.6 g) in collidine (400 ml) at room temperature. When evolution of hydrogen had ceased the mixture was heated under reflux with stirring for 8 hours. It was then cooled and filtered. The residue was washed with ethyl acetate followed by concentrated aqueous ammonia, and the combined filtrate and washings were partitioned between ethyl acetate and water. The organic layer was washed twice with brine and evaporated. The residue was dissolved in ethyl acetate, and the solution was filtered, washed several times with citric acid solution and dried (MgSO4). The solvent was evaporated, and the residue was dissolved in hot hexane. The solution was filtered and the filtrate was evaporated. The residue was chromatographed on silica using hexane as eluent to give the title compound as an oil (18.21 g), Rf 0.31(SS 2). Found: C,41.71; H,1.97. C12H7Br2FO requires C,41.66; H,2.04%.

Fuente