Water → 5-Bromo-2-(methylthio)pyridine

Participants

Reaction Conditions

Reaction Steps

Commercially available 2,5-dibromo pyridine (6.01 g, 25.4 mmol) was dissolved in N,N-dimethylformamide (50 mL), and sodium thiomethoxide (2.20 g, 31.4 mmol) was added, followed by stirring at 0° C. for 3.5 hours under nitrogen atmosphere. The reaction solution was brought back to room temperature, water (250 mL) was added, and extraction was carried out with diethyl ether (250 mL). The organic layer was washed with saturated brine, and subsequently dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate/hexane=3%-5%) to afford the desired compound (4.90 g, yield 94%) as a white solid.

Provenance & Evidence