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

温度

90 °C

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.

1. stirringthe resulting brown mixture was stirred for another 5 h at which time TLC analysis of the mixture
2. temperatureThe reaction mixture was cooled to room temperature
3. customThe two layers were separated
4. extractionthe aqueous layer was extracted with ethyl acetate (50 mL)
5. washThe combined extracts were washed with brine solution (150 mL)
6. dry with materialdried over anhydrous magnesium sulfate
7. filtrationFiltration of the drying agent
8. customthe concentration of the solution under vacuum gave the crude residue which
9. customwas purified
10. washeluting with 0-20% ethyl acetate in hexanes

ORDレコード

ord-21691371418a4b04b8df1acb08b3568f

出典データセット

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08093253B2