Diethyl Ether → O-3-methoxy-5-methylphenyl dimethylcarbamothioate

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To a mixture of 3-methoxy-5-methylphenol (7) (3.39 g, 24.5 mmol) and 1,4-diazabicyclo[2.2.2]octane (5.50 g, 49.0 mmol) in DMF (20 mL) was added dimethylthiocarbamoyl chloride (8) (6.06 g, 49.0 mmol) portionwise. The reaction mixture was stirred at room temperature overnight and 500 mL of ether was added. The organics were washed with water (150 mL), brine (2×50 mL), dried (Na2SO4), and concentrated. Purification by chromatography on silica gel (Hexanes/EtOAc, 4:1) gave O-3-methoxy-5-methylphenyl dimethylcarbamothioate (9) (5.05 g, 91%) as a colourless solid.

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