Réaction #155411

Équation de réaction

4-bromomethylbenzaldehyde

4-hydroxythiophenol

triethylamine

→

title compound

Rendement 62.0%

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

Rendement 62.0%

Solvants

1,4-dioxane

water

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source