반응 #999580

반응 방정식

phenylboronic acid

2,6-dibromonaphthalene

dimethoxyethane

sodium carbonate

→

2-bromo-6-phenyl naphthalene

수율 36.4%

용매

water

water

toluene

반응 조건

후처리

1. 1
   건조dried with magnesium sulfate, toluene
2. 2
   workup.DISTILLATIONwas distilled away under reduced pressure
3. 3
   기타by silica-gel column chromatography and by recrystallizing the residue by hexane

실험 절차

Under an argon gas atmosphere, 128.0 g (1.049 mol) of phenylboronic acid, 300.0 g (1.163 mol) of 2,6-dibromonaphthalene, 24.2 g (21.0 mmol) of tetrakis(triphenylphosphine) palladium(0), 4.3 L of dimethoxyethane and 1.60 L of 2M sodium carbonate solution were mixed, and stirred for 24 hours at 78 degrees C. The reaction mixture was further added with toluene and water, and then aqueous phase thereof was eliminated. After organic phase thereof was cleansed by water and dried with magnesium sulfate, toluene was distilled away under reduced pressure. By refining residue thereof by silica-gel column chromatography and by recrystallizing the residue by hexane, 108 g of 2-bromo-6-phenyl naphthalene was obtained with an yield of 36%.

출처