반응 #155410

반응 방정식

4-fluorobenzaldehyde

3-(methylthio)benzenethiol

potassium carbonate

→

title compound

수율 33.0%

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

수율 33.0%

용매

acetonitrile

water

반응 조건

후처리

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

실험 절차

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.

출처