3-Bromo-4-fluorotoluene → 2-Bromo-4-methyl-1-(methylsulfanyl)benzene

Temperature

125 °C

The 2-bromo-1-fluoro-4-methylbenzene (2.00 g, 10.6 mmol) was dissolved in dimethylacetamide (5.3 mL) and sodium thiomethoxide (0.82 g, 11.6 mmol) was added. The reaction was heated at 125° C. for 5.5 h. The reaction was then cooled to rt and stirred overnight. The reaction was then diluted with water (200 mL) and the mixture was extracted with ethyl acetate (3×125 mL). The combined organic layers were washed with water (1×150 mL) brine (1×100 mL) and dried over magnesium sulfate. The crude product was purified by medium pressure chromatography (silica gel, 0 to 40% EtOAc:hexanes) to give (2-bromo-4-methylphenyl)-(methyl)sulfane. 1H NMR (CDCl3) δ ppm 7.38 (1H, d, J=0.8 Hz), 7.09-7.13 (1H, m), 7.06 (1H, d), 2.47 (3H, s), 2.31 (3H, s).

1. temperatureThe reaction was then cooled to rt
2. extractionthe mixture was extracted with ethyl acetate (3×125 mL)
3. washThe combined organic layers were washed with water (1×150 mL) brine (1×100 mL)
4. dry with materialdried over magnesium sulfate
5. customThe crude product was purified by medium pressure chromatography (silica gel, 0 to 40% EtOAc:hexanes)

ORD record

ord-b25b4e66305b494abc77c93572be6457

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08940724B2