Reaction #554599

Reaction equation

boron boron tribromide

water

2-methoxytriphenylene

→

2-hydroxytriphenylene

Yield 95.1%

Solvents

methylene chloride

methylene chloride

Conditions

Workup

1. 1
   Temperaturewhile increasing temperature of the reaction solution to room temperature
2. 2
   Filtrationfollowed by filtration
3. 3
   WashThe resulting solid was washed with water and methanol

Procedure

Under an argon atmosphere, 13.9 g of 2-methoxytriphenylene was placed in a flask, and 300 mL of methylene chloride was added. The reaction solution was cooled to −78° C., and 54 mL of a solution of 1M boron boron tribromide in methylene chloride was dropwise added thereto. The reaction solution was stirred for 5 hours while increasing temperature of the reaction solution to room temperature. 100 mL of water was added to the reaction solution, followed by filtration. The resulting solid was washed with water and methanol to obtain 12.5 g (yield: 95%) of 2-hydroxytriphenylene.

Source