Reacción #1554021

Ecuación de reacción

triisopropylsilanethiol

sodium hydride

ethyl 3-bromo-4-methylbenzoate

→

title compound

4-Methyl-3-triisopropylsilanylsulfanyl-benzoic acid ethyl ester

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe resulting mixture was warmed
2. 2
   Temperaturato reflux

Procedimiento

To a 0° C. stirred solution of triisopropylsilanethiol (14.28 mmol, 3.07 mL) in THF was added sodium hydride (14.28 mmol, 0.57 g of a 60 wt % dispersion in mineral oil). After 30 min, the mixture was added to a solution of ethyl 3-bromo-4-methylbenzoate (10.99 mmol, 2.67 g) at room temperature, followed by tetrakis(triphenylphosphine)palladium(0) (0.55 mmol, 0.64 g). The resulting mixture was warmed to reflux and stirred for 18 hours, then cooled to room temperature and subjected to standard aqueous workup to afford the title compound which was used crude in the next step.

Fuente