Reaction #1994259

Reaction equation

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

Yield 78.4%

Solvents

methanol

toluene

Conditions

Workup

1. 1
   workup.DISTILLATIONThen, distilled water (40 mL)
2. 2
   workup.ADDITIONwas added
3. 3
   Otherpurified by silica gel
4. 4
   ExtractionThen, a toluene layer was extracted
5. 5
   ConcentrationThe extracted organic solvent was concentrated
6. 6
   Otherremoved
7. 7
   workup.ADDITIONmethanol was added
8. 8
   Otherto produce a solid
9. 9
   FiltrationThrough filtration
10. 10
    Othera yellowish brown solid was obtained

Procedure

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).

Source