Sodium methanethiolate → Pyridine, 5-bromo-2-(methylthio)-3-(trifluoromethyl)-

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Reaction Steps

The product of Example 6 (3.0 g, 0.012 mol) was dissolved with stirring in dimethyl sulphoxide (30 mL) and sodium methanethiolate (1.2 g, 0.017 mol) was added. The mixture was stirred at room temperature overnight, poured into ice-water, and extracted with hexane (2×50 mL). The organic extracts were combined, washed with water and brine, and dried over anhydrous sodium sulphate. Evaporation of the solvent under reduced pressure and purification of the residue by chromatography over silica (10% ethyl acetate:hexane) gave 2-methylthio-3-trifluoromethyl-5-bromopyridine (2.2 g) as a clear oil.

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