Reacción #1005962

Ecuación de reacción

isopropoxyboronic acid pinacol ester

THF

1-bromo-2-ethylsulfanylbenzene

THF

n-butyllithium

→

2-ethylsulfanylphenylboronic acid pinacol ester

Rendimiento 46.0%

Disolventes

Water

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente