Cesium carbonate → 1-Iodo-3-methylsulfanyl-5-nitro-benzene

Participants

Reaction Steps

To a solution of 1-iodo-3,5-dinitrobenzene (15 g, 51 mmole) in 150 mL of DMSO trimethyl(methylthio)silane (10 mL, 70.6 mmol) was added slowly. The resulting reaction mixture turned purple at this point. Cesium carbonate 99.9% (23.13 g, 71.4 mmol) was then added. After stirring at room temperature for 18 h, the reaction mixture was diluted with 150 mL of ether, washed with 400 mL of saturated sodium bicarbonate solution and 150 mL of brine. The combined organic phase were then dried over sodium sulfate, filtered and concentrated under reduced pressure to afford 1-iodo-3-methylsulfanyl-5-nitro-benzene as a yellow solid. The crude material was used in the next step without further purification. HR-EI(+) m/e calcd for C7H6NO2SI (M+) 294.9164, found 294.9164.

Provenance & Evidence