Reaction #155410

Reaction equation

4-fluorobenzaldehyde

3-(methylthio)benzenethiol

potassium carbonate

→

title compound

Yield 33.0%

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

Yield 33.0%

Solvents

acetonitrile

water

Conditions

Workup

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

Procedure

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.

Source