Hydrochloric Acid → (6-Bromo-2-nitropyridin-3-yloxy)acetic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

6-Bromo-2-nitropyridin-3-ol (10.8 g, 49.1 mmol) was dissolved in dimethylsulfoxide (DMSO) (30 mL). Potassium carbonate (13.6 g, 98.6 mmol) and bromoacetic acid methyl ester (7.0 mL, 74 mmol) were added and the reaction mixture was stirred at 60° C. for two hours. Then, the reaction mixture was cooled to room temperature and neutralized with 1N HCl(aq). The aqueous solution was extracted twice with ethyl acetate, and the combined organic extracts were washed with brine. The product was purified by column chromatography (SiO2, EtOAc/hexanes) to afford (6-bromo-2-nitropyridin-3-yloxy)acetic acid methyl ester. Yield 10.9 g (37.5 mmol, 76%). LCMS (ESI): calc. C8H7BrN2O5=290, 292; obs. Low ionization.

Provenance & Evidence