Реакция #155410

Уравнение реакции

4-fluorobenzaldehyde

3-(methylthio)benzenethiol

potassium carbonate

→

title compound

Выход 33.0%

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

Выход 33.0%

Растворители

acetonitrile

water

Условия реакции

Обработка

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

Методика

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.

Источник