Benzene, 1-methyl-3-(methylthio)- → (4-Bromo-3-methylphenyl)(methyl)sulfane

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Reaction Steps

Bromine (2.52 mL, 48.9 mmol) was added dropwise to a solution of 1-methyl-3-(methylthio)benzene (6.14 g, 44.4 mmol) in acetic acid (150 mL) at 0° C. The reaction was then stirred at ambient temperature for 2 h. The reaction was concentrated, and the resulting crude product was purified by chromatography on a silica gel column using 0 to 10% EtOAc/hexane to give 7.94 g (82%) of 1-bromo-2-methyl-4-(methylthio)benzene as a clear oil. 1H NMR (400 MHz, DMSO-d6): δ 7.40 (d, 1H, J=8.3 Hz), 7.10 (d, 1H, J=2.1 Hz), 6.92 (dd, 1H, Ja=8.3 Hz, Jb=2.2 Hz), 2.45 (s, 3H), 2.35 (s, 3H); LRMS (ESI), m/z 218 (M+H).

Provenance & Evidence