반응 #992709

반응 방정식

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

수율 85.5%

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

수율 85.5%

용매

THF

반응 조건

후처리

1. 1
   기타at −78° C
2. 2
   workup.STIRRINGstirred at room temperature for one hour
3. 3
   추출Then an organic layer was extracted with brine and methylene chloride
4. 4
   건조The extracted organic layer was dried with anhydride magnesium sulfate
5. 5
   여과filtered
6. 6
   기타removed of solvent
7. 7
   기타The organic layer was purified through chromatography (silica, hexane)

실험 절차

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.

출처