Reaction #1904046

Reaction equation

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

Yield 38.6%

Solvents

ethanol

Conditions

Workup

1. 1
   TemperatureThen, the mixture was refluxed
2. 2
   workup.STIRRINGwith stirring for 5 hours under nitrogen flow
3. 3
   Temperaturethe reaction mixture was cooled to room temperature
4. 4
   Otherwas separated by filtration
5. 5
   WashThe crystal was washed with acetone
6. 6
   Otherrecrystallized with a mixed solvent of toluene/ethanol
7. 7
   Othercrystallize with methanol

Procedure

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