Boron tribromide → 6-(Pyren-1-yl)biphenyl-3-ol

HRID 1852555Notes

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]=1

Participants

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%).

Workup

customIn a 1000 ml three-necked flask that had been degassed
temperatureThe solution was warmed to room temperature
customto quench unreacted boron tribromide
extractionThe organic layer was extracted with dichloromethane and water
dry with materialdried with anhydrous magnesium sulfate
customthe solvent was removed

Sources & evidence

ORD record: ord-134c29f1eba344b3ae090a1fa35d29b2
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962160B2

Reaction notes

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