Iodine → 6-Bromo-2-iodopyridin-3-OL

Participants

Reaction Steps

A 4.125 g sample of 2-bromo-5-hydroxypyridine (from step 28c) and 5.28 g of Na2CO3 were dissolved in 75 mL of water. To this solution was added 6.02 g of I2, and the mixture was stirred until the iodine color disappeared. The reaction mixture was then adjusted to pH 5, and extracted with EtOAc. The extract was dried over MgSO4, and the solvent was removed. The residue was chromatographed on silica gel, eluting with 97:3 CHCl3 :MeOH to give 4.3 g of the title compound: 1H NMR (CDCl3, 300 MHz) δ 7.08-7.11 (d, 1H, J=8.5 Hz), 7.29-7.32 (d, 1H, J=8.5 Hz); MS m/z: 300 (M+H)+, 317 (M+NH4)+.

Provenance & Evidence