Iodine → 6-Chloro-2-iodo-3-hydroxypyridine

Participants

Reaction Steps

To a solution of 2-chloro-5-hydroxypyridine (5 g, from step 11b) and 8.6 g of Na2CO3 in 100 mL of water was added 9.8 g of I2. 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 recrystallized from MeOH to afford 5.4 g of the title compound: 1H NMR (CD3OD, 300 MHz) δ 7.09 (d, 1H, J=8.5 Hz), 7.20 (d, 1H, J=8.5 Hz); MS m/z: 256 (M+H)+, 273 (M+NH4)+.

Provenance & Evidence