反応 #992709

反応方程式

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

収率 85.5%

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

収率 85.5%

溶媒

THF

反応条件

後処理

1. 1
   その他at −78° C
2. 2
   workup.STIRRINGstirred at room temperature for one hour
3. 3
   抽出Then an organic layer was extracted with brine and methylene chloride
4. 4
   乾燥The extracted organic layer was dried with anhydride magnesium sulfate
5. 5
   ろ過filtered
6. 6
   その他removed of solvent
7. 7
   その他The organic layer was purified through chromatography (silica, hexane)

実験手順

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.

出典