Methanol → Methyl 3-bromo-2-pyridinecarboxylate

Participants

Reaction Conditions

Reaction Steps

To a mixture of 3-bromo-2-cyano-pyridine (13.53 g; 73.93 mmol) in 150 ml of methanol was added 25% NaOH solution (250 ml) and the resulting mixture was refluxed for 3 hours, cooled, and concentrated in vacuo. The residue was dissolved in 350 ml of methanol, cooled to 0° C. 250 ml of methanolic HCl solution was added portionwise, and the mixture was refluxed for 17 hours. The reaction mixture was cooled to 0° C. neutralized with triethylamine, concentrated in vacuo, and the residue partitioned between ethyl acetate (800 ml)/water (300 ml). The organic layer was washed with brine, dried over sodium sulfate, and concentrated in vacuo to afford 12.85 g (80.5%) of methyl 3-bromo-pyridine-2-carboxylate.

Provenance & Evidence