Dibromomethane → 3-(2-[1,3]Dithietan-2-ylidene-2-pyridin-4-yl-acetyl)-benzonitrile

Participants

Reaction Steps

To a solution of 3-(pyridin-4-yl-acetyl)-benzonitrile (12.5 g, 56 mmol) in dry DMSO (280 mL) under nitrogen atmosphere solid potassium carbonate (23.36 g, 169 mmol, 3 eq) was added at room temperature, followed by carbon disulfide (10.2 mL, 169 mmol, 3 eq) and dibromomethane (11.86 mL, 169 mmol, 3 eq). The reaction mixture was stirred at room temperature for 2 hours and then poured into stirred iced water (1.5 L mL). The orange precipitate was filtered, washed with water and dried at 60° C. under reduced pressure for 1 hour. The crude product was purified by silica gel chromatography (SP1, eluant: n-hexane/ethyl acetate 2:8) to obtain 10.1 g of yellow solid (58%).

Provenance & Evidence