Reacción #1994257

Ecuación de reacción

9,10-dihydroacridine

4-bromobiphenyl

→

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

Rendimiento 70.4%

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONThen, NaOBut (9.4 g, 97.8 mmol) was added
2. 2
   Lavadowas washed with MC
3. 3
   OtroThe filtrate was evaporated under a reduced pressure
4. 4
   Otroto remove the solvent
5. 5
   OtroThe residue was then purified by silica gel column chromatography (methylene chloride/n-hexane (1/10))

Procedimiento

The obtained 9,10-dihydroacridine (11.8 g, 65.2 mmol) and 4-bromobiphenyl (18.2 g, 78.2 mmol) were dissolved in toluene (500 mL). Then, Pd2(dba)3 (1.4 g, 1.3 mmol) was added thereto under a nitrogen atmosphere. Then, NaOBut (9.4 g, 97.8 mmol) was added thereto, and (t-Bu)3P (1.6 ml, 2.6 mmol) was introduced to the resultant solution. The resultant mixture was reflux-stirred for 5 hours. The completion of the reaction was identified by a TLC. After the reaction was completed, the mixture was cooled to room temperature. The resultant solution was poured onto a thin silica pad so as to perform a short chromatography, and then was washed with MC. The filtrate was evaporated under a reduced pressure to remove the solvent. The residue was then purified by silica gel column chromatography (methylene chloride/n-hexane (1/10)) to obtain 10-(biphenyl-4-yl)-9,10-dihydroacridine compound (pale yellow solid, 15.3 g, yield 70%).

Fuente