Iodine → 2-Bromo-6-iodopyridin-3-ol

Participants

Reaction Steps

To a solution of 2-bromopyridin-3-ol (1.00 g, 5.80 mmol) in water (30 mL) was added Na2CO3 (1.23 g, 11.60 mmol) and I2 (1.53 g, 5.80 mmol). After 1 hour, the reaction was quenched with 1 N HCl (20 mL), extracted with EtOAc (2×100 mL), and washed with aq. NaHSO3 and brine (50 mL each). The organic layer was dried over Na2SO4, filtered and concentrated. Purification of the residue by flash chromatography on silica gel (20 to 40% EtOAc/hexanes) afforded 2-bromo-6-iodopyridin-3-ol. Rf=0.44 (25% EtOAc/hexanes). LCMS=301.9 (M+1)+. 1H NMR (CDCl3, 500 MHz) δ 7.56 (d, J=8.3 Hz, 1H), 6.99 (d, J=8.3 Hz, 1H), 5.65 (s, 1H).

Provenance & Evidence