Reacción #155411

Ecuación de reacción

4-bromomethylbenzaldehyde

4-hydroxythiophenol

triethylamine

→

title compound

Rendimiento 62.0%

4-{[(4-Hydroxyphenyl)thio]methyl}benzaldehyde

Rendimiento 62.0%

Disolventes

1,4-dioxane

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted with ethyl acetate (2-fold 20 mL)
2. 2
   LavadoThe combined organic extracts were washed with brine
3. 3
   Secadodried (sodium sulphate)
4. 4
   Otrothe solvent removed in vacuo
5. 5
   OtroThe crude material was purified by flash column chromatography on silica gel eluting with heptane:ethyl acetate (9:1 changing to 0:1, by volume)

Procedimiento

A solution of 4-bromomethylbenzaldehyde (0.3 g, 1.5 mmol) and 4-hydroxythiophenol (0.2 g, 1.5 mmol) in 1,4-dioxane (10 mL) was degassed and treated with triethylamine (0.44 mL, 3.11 mmol). After stirring for 1 day the mixture was diluted with water (20 mL) and extracted with ethyl acetate (2-fold 20 mL). The combined organic extracts were washed with brine and dried (sodium sulphate) and the solvent removed in vacuo. The crude material was purified by flash column chromatography on silica gel eluting with heptane:ethyl acetate (9:1 changing to 0:1, by volume) to give the title compound as a solid, 62% yield, 220 mg.

Fuente