Iodine → HCID 58415369, compound

Participants

Reaction Steps

5-benzyl-6-chloropyridin-3-ol (0.73 g, 3.3 mmol) and I2 (0.21 mL, 4.0 mmol). The mixture became homogeneous and yellow after stirring for 16 h. The mixture was washed with sodium thiosulfate (100 mL), and then treated cautiously with conc. HCl until the pH was 2 by pH paper. The solution was extracted with EtOAc (3×50 mL), and the combined organic extracts were dried over MgSO4, filtered and concentrated to afford a pale yellow solid. The solid was purified by triturating with minimal DCM and ether to give a beige solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 10.90-11.09 (1H, br s), 7.30-7.37 (2H, m), 7.17-7.28 (3H, m), 6.99 (1H, s), 3.95 (2H, s); MS (ESI) m/z: Calculated: 344.9; Observed: 345.9 (M++1).

Provenance & Evidence