Bromine → Methyl 6-bromo-3-hydroxypicolinate

Participants

Reaction Steps

A solution of methyl 3-hydroxypicolinate (5 g, 32.65 mmol) in 60 mL of H2O was stirred at RT and Br2 (5.22 g, 32.65 mmol) was added dropwise. The mixture was stirred at RT overnight, and the resulting solid was collected and washed with water to afford methyl 6-bromo-3-hydroxypicolinate. Then the filtrate was basified with Na2CO3 until pH reached 7, and after extracted with EtOAc, the organic layer was concentrated to give the 2nd part of methyl 6-bromo-3-hydroxypicolinate (6.1 g total, yield: 80.7%). 1H-NMR (CDCl3, 400 MHz) δ 10.67 (s, 1H), 7.54 (t, J=8.0 Hz, 1H), 7.24 (d, J=4.0 Hz, 1H), 4.02 (s, 3H). MS (M+H)+: 232/234.

Provenance & Evidence