Bromine → Methyl 4,6-dibromo-3-hydroxypicolinate

Participants

Reaction Steps

To a magnetically stirred solution of methyl 2-amino-2-(furan-2-yl)acetate hydrobromide (0.84 g, 3.56 mmol) and sodium acetate (1.255 g, 15.30 mmol) in 40 mL of water at 0° C. was added dropwise a solution of bromine (0.788 ml, 15.30 mmol) in 10 mL of MeOH over 30 min. After warming to room temperature for 24 hr, the reaction mixture was filtered through a fritted glass funnel and the white solid was washed with water. Solvent removal gave methyl 4,6-dibromo-3-hydroxypicolinate (577 mg, 1.837 mmol, 51.6% yield) as a white solid; Mp 180-181° C. (recrystallized from heptane). 1H NMR (600 MHz, Chloroform-d) δ 11.35 (s, 1H), 7.86 (s, 1H), 4.07 (s, 3H); 13C NMR (151 MHz, Chloroform-d) δ 168.74, 156.02, 136.85, 130.14, 129.92, 124.67, 53.84. HRMS-ESI (m/z) calc'd for [C7H5Br2NO3]+, 308.8636. found, 308.8638.

Provenance & Evidence