Réaction #1005962

Équation de réaction

isopropoxyboronic acid pinacol ester

THF

1-bromo-2-ethylsulfanylbenzene

THF

n-butyllithium

→

2-ethylsulfanylphenylboronic acid pinacol ester

Rendement 46.0%

Solvants

Water

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source