Reaction #1458418

Reaction equation

(2,4,6-triisopropylphenyl)dimethoxyborane

magnesium bromide

4,4′-dibromo-2,2′-diiodo-5,5′-dioctyloxy-1,1′-biphenyl

hexane

→

3,7-dibromo-5-(2,4,6-triisopropylphenyl)-2,8-dioctyloxy-5H-dibenzo(b, d)borole

Solvents

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   workup.DISSOLUTIONto dissolve the same
3. 3
   workup.STIRRINGstirred for 1 hour
4. 4
   TemperatureThe mixture was cooled again to −90° C.
5. 5
   TemperatureAfter warming
6. 6
   Otherto react
7. 7
   Temperatureunder reflux for 12 hours

Procedure

2.0 g of 4,4′-dibromo-2,2′-diiodo-5,5′-dioctyloxy-1,1′-biphenyl synthesized as above was put in a 100 ml flask in an atmosphere of nitrogen and 20 ml of tetrahydrofuran was added to dissolve the same. Then, the tetrahydrofuran solution was cooled to −90° C. and 3.4 ml of 1.6M hexane solution was added dropwise. After 1-hour stirring, a solution of 1.5 g of magnesium bromide in 20 ml of tetrahydrofuran was added, warmed to room temperature, and stirred for 1 hour. The mixture was cooled again to −90° C., and 1.01 g of (2,4,6-triisopropylphenyl)dimethoxyborane was added. After warming, the mixture was allowed to react under reflux for 12 hours.

Source