Methanol → 3-Bromo-5-methoxypyridine

Participants

Reaction Conditions

Reaction Steps

Add sodium (0.583 g, 25 mmol) to methanol (10 mL) at 0° C. Stir the mixture at 0° C. until obtain a solution and concentrate. Add N,N-dimethylformamide (25 mL) and add 3,5-dibromopyridine (3.0 g, 12.66 mmol). Stir at 70° C. for 4 h. Cool to room temperature and add water. Extract twice with diethyl ether. Combine the organic phases, wash once with water, dry over sodium sulfate and concentrate. Purify the residue by silica gel chromatography, eluting with a gradient of 100:0 to 50:50 hexanes:ethyl acetate, to give the title compound as a solid (1.37 g, 57%).

Provenance & Evidence