Dimethylformamide → Methyl 2-methyl-3-(methylthio)benzoate

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Reaction Steps

A mixture of 3-mercapto-2-methylbenzoic acid (180 mg, 1.05 mmol), cesium carbonate (690 mg, 2.1 mmol) and iodomethane (132 L1, 2.10 mmol) in dimethylformamide (3 mL) was stirred at room temperature for 2 hours. The mixture was diluted with ethyl acetate then washed with 5% aqueous lithium chloride, 1N aqueous sodium hydroxide, and brine then dried over anhydrous sodium sulfate. Filtration and concentration afforded 138 mg, 0.62 mmol (58%) of methyl 2-methyl-3-(methylthio)benzoate. 1H NMR (400 MHz, CDCl3): 7.58 (d, 1H), 7.41 (d, 1H), 7.21-7.16 (m, 1H), 4.09 (s, 3H), 2.83 (s, 3H), 2.58 (s, 3H). MS (EI) for C10H12SO2: 197 (MH+).

Provenance & Evidence