2-Bromothioanisole

• thioether-methyleneborane (PhSCH₂B (C₆F₅)₂)₂
• 1-dimesitylboryl-2-methylthio-benzene

6320-02-1

74-88-4

19614-16-5

Under argon protection, sodium hydroxide (0.32 g, 7.9 mmol) was dissolved in ethanol (3.0 mL), and 2-bromothiophenol (1.0 g, 5.29 mmol) was added slowly and stirred for 30 min at room temperature. Subsequently, iodomethane (0.5 mL, 7.9 mmol) was added and the reaction continued to be stirred at room temperature for 3 hours. Upon completion of the reaction, the reaction was quenched by the addition of ice water (4.0 mL) and the reaction mixture was extracted with dichloromethane (10 mL x 3). The organic layers were combined, washed with saturated saline, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by fast column chromatography (eluent: petroleum ether) to afford the target compound 2-bromothioanisole.