تفاعل #992709

معادلة التفاعل

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

المردود 85.5%

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

المردود 85.5%

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   أخرىat −78° C
2. 2
   workup.STIRRINGstirred at room temperature for one hour
3. 3
   استخلاصThen an organic layer was extracted with brine and methylene chloride
4. 4
   تجفيفThe extracted organic layer was dried with anhydride magnesium sulfate
5. 5
   ترشيحfiltered
6. 6
   أخرىremoved of solvent
7. 7
   أخرىThe organic layer was purified through chromatography (silica, hexane)

الإجراء التجريبي

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.

المصدر