반응 #81602

반응 방정식

hydrogen

Sodium hydride

1,3,5-tribromobenzene

4-fluorophenol

→

title compound

수율 32.5%

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

수율 32.5%

용매

collidine

반응 조건

후처리

1. 1
   온도was heated
2. 2
   온도under reflux
3. 3
   온도It was then cooled
4. 4
   여과filtered
5. 5
   세척The residue was washed with ethyl acetate
6. 6
   기타the combined filtrate and washings were partitioned between ethyl acetate and water
7. 7
   세척The organic layer was washed twice with brine
8. 8
   기타evaporated
9. 9
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate
10. 10
    여과the solution was filtered
11. 11
    세척washed several times with citric acid solution
12. 12
    건조dried (MgSO4)
13. 13
    기타The solvent was evaporated
14. 14
    workup.DISSOLUTIONthe residue was dissolved in hot hexane
15. 15
    여과The solution was filtered
16. 16
    기타the filtrate was evaporated
17. 17
    기타The residue was chromatographed on silica

실험 절차

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%.

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