反应 #1005962

反应方程式

isopropoxyboronic acid pinacol ester

THF

1-bromo-2-ethylsulfanylbenzene

THF

n-butyllithium

→

2-ethylsulfanylphenylboronic acid pinacol ester

收率 46.0%

溶剂

Water

反应条件

后处理

1. 1
   温度to maintain an internal temperature of −60° C.
2. 2
   workup.ADDITIONwas added to the mixture at a rate so as
3. 3
   温度to maintain an internal temperature of −60° C.
4. 4
   温度lower, and the mixture was heated to room temperature
5. 5
   萃取the mixture was extracted with ethyl acetate
6. 6
   洗涤The organic layer was washed with water
7. 7
   干燥dried over anhydrous sodium sulfate
8. 8
   浓缩concentrated under reduced pressure

实验过程

A mixture of 14.1 g of 1-bromo-2-ethylsulfanylbenzene and 65 mL of THF was cooled to −70° C., and 44.7 mL of n-butyllithium (1.63 M hexane solvent) was added to the mixture at a rate so as to maintain an internal temperature of −60° C. or lower, and the mixture was stirred at −50° C. for 30 minutes. A mixture of 14 g of isopropoxyboronic acid pinacol ester and 5 mL of THF was added to the mixture at a rate so as to maintain an internal temperature of −60° C. or lower, and the mixture was heated to room temperature. Water was poured to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, then dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was applied to a silica gel column chromatography to obtain 7.9 g of 2-ethylsulfanylphenylboronic acid pinacol ester.

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