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, 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).

Provenance & Evidence