Reacción #155410

Ecuación de reacción

4-fluorobenzaldehyde

3-(methylthio)benzenethiol

potassium carbonate

→

title compound

Rendimiento 33.0%

4-{[3-(Methylthio)phenyl]thio}benzaldehyde

Rendimiento 33.0%

Disolventes

acetonitrile

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted with ethyl acetate (3-fold 300 mL)
2. 2
   LavadoThe combined organic extracts were washed with brine (2-fold 100 mL)
3. 3
   Secadodried (magnesium sulphate)
4. 4
   Otrothe solvent removed in vacuo
5. 5
   Otroto give a colourless oil
6. 6
   OtroThe crude oil was purified by flash column chromatography on silica gel eluting with heptane:ethyl acetate (1:0 changing to 9:1, by volume)

Procedimiento

A solution of 3-(methylthio)benzenethiol (19.9 g, 127.3 mmol), prepared as indicated in Rumpf, P., Bull. soc. chim. (1940), 7, pp. 632-4, in acetonitrile (60 mL) was treated with 4-fluorobenzaldehyde (13.4 mL, 127 mmol) followed by potassium carbonate (19.4 g, 140 mmol). After stirring at ambient temperature for 18 hours the suspension was diluted with water (200 mL) and extracted with ethyl acetate (3-fold 300 mL). The combined organic extracts were washed with brine (2-fold 100 mL) and dried (magnesium sulphate) and the solvent removed in vacuo to give a colourless oil. The crude oil was purified by flash column chromatography on silica gel eluting with heptane:ethyl acetate (1:0 changing to 9:1, by volume) to give the title compound as a colourless oil, 33% yield, 10.8 g.

Fuente