Boron tribromide → 6-(Pyren-1-yl)biphenyl-3-ol
Reaction equation
C[O:2][C:3]1[CH:4]=[CH:5][C:6]([C:15]2[C:28]3[C:29]4=[C:30]5[C:25](=[CH:26][CH:27]=3)[CH:24]=[CH:23][CH:22]=[C:21]5[CH:20]=[CH:19][C:18]4=[CH:17][CH:16]=2)=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:8]=1.B(Br)(Br)Br>ClCCl>[C:15]1([C:6]2[C:7]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[CH:8][C:3]([OH:2])=[CH:4][CH:5]=2)[C:28]2[C:29]3=[C:30]4[C:25](=[CH:26][CH:27]=2)[CH:24]=[CH:23][CH:22]=[C:21]4[CH:20]=[CH:19][C:18]3=[CH:17][CH:16]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
In a 1000 ml three-necked flask that had been degassed and filled with nitrogen, 12.4 g (32.2 mmol) of 1-(5-methoxybiphenyl-2-yl)pyrene was dissolved in anhydrous dichloromethane (200 ml), the solution was cooled to −78° C., and 24.2 g (96.6 mmol) boron tribromide was added slowly. The solution was warmed to room temperature and stirred overnight. 200 g Ice was carefully added to quench unreacted boron tribromide. The organic layer was extracted with dichloromethane and water, dried with anhydrous magnesium sulfate, the solvent was removed to give product 10.8 g (91%).