Reacción #992709

Ecuación de reacción

water

n-BuLi

6-bromo-2,3-di-p-tolyl-benzo[b]thiophene

2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

→

white solid

Rendimiento 85.5%

2-(2,3-di-p-tolyl-benzo[b]thiophen-6-yl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

Rendimiento 85.5%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroat −78° C
2. 2
   workup.STIRRINGstirred at room temperature for one hour
3. 3
   ExtracciónThen an organic layer was extracted with brine and methylene chloride
4. 4
   SecadoThe extracted organic layer was dried with anhydride magnesium sulfate
5. 5
   Filtraciónfiltered
6. 6
   Otroremoved of solvent
7. 7
   OtroThe organic layer was purified through chromatography (silica, hexane)

Procedimiento

Under argon atmosphere, in a 500 ml round-bottomed flask, 5 g (12.75 mmol) of 6-bromo-2,3-di-p-tolyl-benzo[b]thiophene was dissolved in 150 ml of THF, and 6.12 ml (15.31 mmol) of n-BuLi 2.5M (hexane) was added thereto at −78° C. The resulting solution was stirred at −78° C. for 2 hours. Then 3.4 ml (16.58 mmol) of 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was added thereto and stirred at room temperature for one hour. The reaction was ended by adding 50 ml of water. Then an organic layer was extracted with brine and methylene chloride. The extracted organic layer was dried with anhydride magnesium sulfate, filtered and removed of solvent. The organic layer was purified through chromatography (silica, hexane), and 4.8 g (yield 79%) of white solid product was obtained by increasing the polarity of the developing solvent.

Fuente