Sodium Iodide → 3-Bromo-6-iodo-2-methylpyridine

Participants

Reaction Conditions

Reaction Steps

Sodium iodide (2 equiv) and 3,6-dibromo-2-methylpyridine (1 equiv) were combined in propionitrile and the resulting slurry was treated with iodotrimethylsilane (0.2 equiv) and heated to 95° C., with stirring, under nitrogen for 24 h. The slurry was cooled to room temperature, diluted with a 1:1 mixture of ethyl acetate and water and the aqueous and organic phases were separated. The organic layer was washed with saturated aqueous sodium bicarbonate solution, sodium thiosulfate (5% aqueous solution), and saturated aqueous sodium chloride solution. The organic phase was dried, filtered, and concentrated under reduced pressure to afford the desired product, as an oil, which crystallized to a solid. MS (ESI) m/z 297.8 [M]+, 299.8 [M+2]+.

Provenance & Evidence