Reacción #1994259

Ecuación de reacción

methylene chloride

potassium carbonate

phenyl boronic acid

10-(biphenyl-4-yl)-2-bromo-9,10-dihydroacridine

→

10-(biphenyl-4-yl)-2-phenyl-9,10-dihydroacridine

Rendimiento 78.4%

Disolventes

methanol

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.DISTILLATIONThen, distilled water (40 mL)
2. 2
   workup.ADDITIONwas added
3. 3
   Otropurified by silica gel
4. 4
   ExtracciónThen, a toluene layer was extracted
5. 5
   ConcentraciónThe extracted organic solvent was concentrated
6. 6
   Otroremoved
7. 7
   workup.ADDITIONmethanol was added
8. 8
   Otroto produce a solid
9. 9
   FiltraciónThrough filtration
10. 10
    Otroa yellowish brown solid was obtained

Procedimiento

10-(biphenyl-4-yl)-2-bromo-9,10-dihydroacridine compound (10 g, 24.3 mmol) was dissolved in toluene (300 mL) under a nitrogen atmosphere. Then, phenyl boronic acid (3.6 g, 29.2 mmol) was added thereto. To the resultant mixture solution, tetrakis triphenyl phosphine palladium (1.1 g, 0.97 mmol) and potassium carbonate (10.1 g, 72.9 mmol) were added. Then, distilled water (40 mL) was added thereto, followed by reflux-stirring for 3 hours. The resultant solution was cooled to about 60° C., and purified by silica gel. Then, a toluene layer was extracted. The extracted organic solvent was concentrated and removed, and methanol was added to produce a solid. Through filtration, a yellowish brown solid was obtained. It was dissolved by methylene chloride, and added with methanol in small amounts so as to obtain required 10-(biphenyl-4-yl)-2-phenyl-9,10-dihydroacridine compound (7.8 g, yield 78%, pale yellow solid).

Fuente