Réaction #992709

Équation de réaction

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

Rendement 85.5%

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

Rendement 85.5%

Solvants

THF

Conditions de réaction

Traitement

1. 1
   Autreat −78° C
2. 2
   workup.STIRRINGstirred at room temperature for one hour
3. 3
   ExtractionThen an organic layer was extracted with brine and methylene chloride
4. 4
   SéchageThe extracted organic layer was dried with anhydride magnesium sulfate
5. 5
   Filtrationfiltered
6. 6
   Autreremoved of solvent
7. 7
   AutreThe organic layer was purified through chromatography (silica, hexane)

Mode opératoire

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.

Source