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

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 4-bromo-2-fluoro-1-methyl-benzene (3 mL, 26.3 mmol) in DMF (15 mL) was added MeSNa (1.84 g, 26.3 mmol). After the addition, the reaction mixture was stirred at 90° C. overnight. TLC (petroleum) showed the reaction was complete. Then the mixture was poured into aq. NaHCO3 (10 mL), extracted with EtOAc (20 mL×2). The combined organic layers were washed with brine (50 mL×3), dried over sodium sulfate and concentrated in vacuum. The residue was purified by a silica gel column chromatography (petroleum) to give 4-Bromo-1-methyl-2-methylsulfanyl-benzene (4 g, 68%) as a yellow liquid.

Provenance & Evidence