Methanol → Methyl 3-bromo-2-pyridinecarboxylate

Temperature

0 °C

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.

1. temperaturethe resulting mixture was refluxed for 3 hours
2. temperaturecooled
3. concentrationconcentrated in vacuo
4. dissolutionThe residue was dissolved in 350 ml of methanol
5. addition250 ml of methanolic HCl solution was added portionwise
6. temperaturethe mixture was refluxed for 17 hours
7. temperatureThe reaction mixture was cooled to 0° C.
8. concentrationconcentrated in vacuo
9. customthe residue partitioned between ethyl acetate (800 ml)/water (300 ml)
10. washThe organic layer was washed with brine
11. dry with materialdried over sodium sulfate
12. concentrationconcentrated in vacuo

ORD record

ord-6d7ff84b0f3447bab81cd7d2015ad145

Source dataset

uspto-grants-1996_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05556909