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

Temperature

125 °C

The 2-bromo-1-fluoro-4-methylbenzene (2.00 g, 11.0 mmol) was dissolved in dimethylacetamide (5.3 mL) followed by the addition of sodium thiomethoxide (0.82 g, 12.0 mmol). 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 EtOAc (3×125 mL). The combined organic layers were washed with water (1×150 mL) and brine (1×100 mL) and dried over MgSO4. The crude product was purified by column chromatography (silica gel, 0 to 40% EtOAc:hexanes) to give (2-bromo-4-methylphenyl)-(methyl)sulfane. 1H NMR (400 MHz, chloroform-d) 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 EtOAc (3×125 mL)
3. washThe combined organic layers were washed with water (1×150 mL) and brine (1×100 mL)
4. dry with materialdried over MgSO4
5. customThe crude product was purified by column chromatography (silica gel, 0 to 40% EtOAc:hexanes)

ORD record

ord-60898ec7ae024f20bc4ba44c0d311e42

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08765940B2