Dimethylformamide → 1-Bromo-3-(ethylthio)-5-methoxybenzene

Temperature

105 °C

To a mixture 1,3-dibromo-5-methoxy-benzene (2.65 g, 10 mmol) and sodium thioethoxide (1.01 g, 12 mmol) was added dimethylformamide (30 mL) at room temperature. Then, the resulting light yellow solution was heated to 105° C. and stirred for 2 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 (50 mL) and brine solution (50 mL). Then, the organic compound was extracted into ethyl acetate (3×50 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 reduced pressure gave the crude residue which was purified by using an ISCO 120 g column chromatography, eluting with 0-20% ethyl actetate in hexanes to obtain 1-bromo-3-ethylsulfanyl-5-methoxy-benzene (1.35 g, 55%) as a white solid: EI(+)-HRMS m/e calcd for C9H11BrOS (M)+ 245.9715, found 245.9713.

1. temperatureThe reaction mixture was cooled to room temperature
2. extractionThen, the organic compound was extracted into ethyl acetate (3×50 mL)
3. washThe combined extracts were washed with brine solution (150 mL)
4. dry with materialdried over anhydrous magnesium sulfate
5. filtrationFiltration of the drying agent
6. customthe concentration of the solution under reduced pressure gave the crude residue which
7. customwas purified
8. washeluting with 0-20% ethyl actetate in hexanes

ORD record

ord-016d37873ec34790b52be2736d976af9

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08093253B2