2,5-Dibromopyridine → 5-Bromo-2-(methylthio)pyridine

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Reaction Steps

To a solution of 2,5-Dibromo-pyridine (6 g, 25.327 mmol) in DMF (60 mL) is added sodium thiomethoxide (1.95 g, 27.86 mmol) at 0° C. Reaction mixture is allowed to come to room temperature and resulting reaction mixture is stirred at room temperature for 12 h. Reaction mixture is quenched with water and extracted with ethyl acetate. Organic layer is dried over sodium sulphate, concentrated and purified by column chromatography using silica (100-200) mesh size and using 4% ethyl acetate in hexane as an eluent to get (4.5 g) of yellow solid title compound. 1H-NMR (400 MHz, DMSO) δ: 2.49 (s, 3H), 7.29 (d, 1H, J=8.76 Hz), 7.85-7.88 (dd, 1H, J1=2.44 Hz, J2=8.48 Hz), 8.55 (d, 1H, J=2.4 Hz). LC-MS (m/z): M+H=206.1.

Provenance & Evidence