반응 #167470

반응 방정식

9-bromoanthracene

phenylboronic acid

potassium carbonate

tris(o-tolyl)phosphine

→

9-phenylanthracene

수율 85.0%

용매

ethylene glycol dimethyl ether

반응 조건

후처리

1. 1
   기타Into a 200 mL three-neck flask were put
2. 2
   여과After the stirring, a precipitated solid was collected by suction filtration
3. 3
   workup.DISSOLUTIONdissolved in toluene
4. 4
   여과filtered through Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135), Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), and alumina
5. 5
   세척The obtained filtrate was washed with water and saturated saline
6. 6
   건조by drying with magnesium sulfate
7. 7
   여과filtered
8. 8
   농축the obtained filtrate was concentrated
9. 9
   기타the object of the synthesis
10. 10
    기타was obtained in a yield of 85% (synthesis scheme (X-1))

실험 절차

Into a 200 mL three-neck flask were put 5.4 g (21 mmol) of 9-bromoanthracene, 2.6 g (21 mmol) of phenylboronic acid, 60 mg (0.2 mmol) of palladium(II) acetate (abbr.: Pd(OAc)2), 10 mL (20 mmol) of potassium carbonate solution (2.0 mol/L), 260 mg (0.8 mmol) of tris(o-tolyl)phosphine (abbr.: P(o-tolyl)3), and 20 mL of ethylene glycol dimethyl ether, and then the mixture was stirred at 80° C. under a nitrogen stream for 9 hours. After the stirring, a precipitated solid was collected by suction filtration, dissolved in toluene, and filtered through Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135), Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), and alumina. The obtained filtrate was washed with water and saturated saline, followed by drying with magnesium sulfate. This suspending solution was gravity filtered and the obtained filtrate was concentrated, whereby 22 g of a light-brown solid of 9-phenylanthracene, which was the object of the synthesis, was obtained in a yield of 85% (synthesis scheme (X-1)).

출처