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

Participants

Reaction Conditions

Reaction Steps

To a solution of 3,5-dinitroanisole (5.0 g, 25.23 mmol) in dimethylsulfoxide (50 mL) were added methylthiotrimethylsilane (4.86 g, 40.37 mmol) and cesium carbonate (16.61 g, 50.46 mmol) at room temperature. The resulting dark green solution was stirred for 15 h at this temperature. Then, the reaction mixture was heated to 90° C. and the resulting brown mixture was stirred for another 5 h at which time TLC analysis of the mixture indicated the absence of starting material. The reaction mixture was cooled to room temperature and diluted with water (100 mL) and ethyl acetate (100 mL). The two layers were separated and the aqueous layer was extracted with ethyl acetate (50 mL). The combined extracts were washed with brine solution (150 mL) and dried over anhydrous magnesium sulfate. Filtration of the drying agent and the concentration of the solution under vacuum gave the crude residue which was purified by using an ISCO 120 column chromatography, eluting with 0-20% ethyl acetate in hexanes to obtain 1-methoxy-3-methylsulfanyl-5-nitro-benzene (1.44 g, 28.6%) as an yellow solid: EI(+)-HRMS m/e calcd for C8H9NO3S (M)+ 199.0303, found 199.0294.

Provenance & Evidence