Réaction #1904046

Équation de réaction

toluene

4-(2-phenylindole-1-yl)phenyl boronic acid

9-(4-bromophenyl)carbazole

sodium carbonate

→

4-(2-phenylindole-1-yl)-4′-(carbazole-9-yl)biphenyl

Rendement 38.6%

Solvants

ethanol

Conditions de réaction

Traitement

1. 1
   TempératureThen, the mixture was refluxed
2. 2
   workup.STIRRINGwith stirring for 5 hours under nitrogen flow
3. 3
   Températurethe reaction mixture was cooled to room temperature
4. 4
   Autrewas separated by filtration
5. 5
   LavageThe crystal was washed with acetone
6. 6
   Autrerecrystallized with a mixed solvent of toluene/ethanol
7. 7
   Autrecrystallize with methanol

Mode opératoire

0.78 g (2.49 mmole) of 4-(2-phenylindole-1-yl)phenyl boronic acid and 0.80 g (2.48 mmole) of 9-(4-bromophenyl)carbazole were put in a 20 ml three-necked flask, and 2.5 ml of toluene, 1.5 ml of ethanol, and 2.5 ml of 2M-sodium carbonate solution were put therein, and 0.09 g (0.08 mmole) of tetrakis-(triphenylphosphine) palladium (0) was added under stirring at room temperature under nitrogen flow. Then, the mixture was refluxed with stirring for 5 hours under nitrogen flow. After the reaction was completed, the reaction mixture was cooled to room temperature and deposited crystal was separated by filtration. The crystal was washed with acetone and recrystallized with a mixed solvent of toluene/ethanol. The obtained crystal was refined by alumina column chromatography (eluent:toluene) and crystallize with methanol to give 0.49 g of a white crystal of 4-(2-phenylindole-1-yl)-4′-(carbazole-9-yl)biphenyl (Exemplary Compound No. 34)(yield: 38.6%).

Source