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

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence