반응 #1005962

반응 방정식

isopropoxyboronic acid pinacol ester

THF

1-bromo-2-ethylsulfanylbenzene

THF

n-butyllithium

→

2-ethylsulfanylphenylboronic acid pinacol ester

수율 46.0%

용매

Water

반응 조건

후처리

1. 1
   온도to maintain an internal temperature of −60° C.
2. 2
   workup.ADDITIONwas added to the mixture at a rate so as
3. 3
   온도to maintain an internal temperature of −60° C.
4. 4
   온도lower, and the mixture was heated to room temperature
5. 5
   추출the mixture was extracted with ethyl acetate
6. 6
   세척The organic layer was washed with water
7. 7
   건조dried over anhydrous sodium sulfate
8. 8
   농축concentrated under reduced pressure

실험 절차

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.

출처