ethyl 5-broMo-6-Methylnicotinate Chemical Properties

Boiling point:

270.5±35.0 °C(Predicted)

Density 

1.439±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

pka

1.66±0.20(Predicted)

ethyl 5-broMo-6-Methylnicotinate Usage And Synthesis

Synthesis

To an oven-dried resealable Schlenk tube, ethyl 5,6-dibromonicotinate (1.09 g, 3.5 mmol), methylboronic acid (0.24 g, 4.0 mmol), potassium carbonate (1.46 g, 10.6 mmol), and 1,4-dioxane (27 mL) were added sequentially. Three evacuation-argon backfill cycles were performed on the Schlenk tubes, followed by the addition of tetrakis(triphenylphosphine)palladium(0) (0.41 g, 0.35 mmol). After three more evacuation-argon backfill cycles, the Schlenk tube was sealed and the reaction mixture was placed in an oil bath and the reaction was stirred at 110 °C. After 3 days of reaction, the mixture was cooled and filtered through Celite. The filtrate was concentrated under reduced pressure and the residue was purified by fast column chromatography (eluent ratio: 97:3 to 9:1 hexane/ethyl acetate) to afford the target product ethyl 5-bromo-6-methylnicotinate (0.41 g, 45% yield) as a solid.LRMS (m/z): 244/246 (M + 1)+.1H-NMR δ (CDCl3): 1.41 (t, J = 9.0 Hz, 3H), 2.74 (s, 3H), 4.41 (q, J = 9.0 Hz, 2H), 8.40 (d, J = 3.0 Hz, 1H), 9.01 (d, J = 3.0 Hz, 1H).

References

[1] Patent: EP2108641, 2009, A1. Location in patent: Page/Page column 55-56

ethyl 5-broMo-6-Methylnicotinate(1190862-70-4)Related Product Information

• 5-broMo-6-Methoxynicotinaldehyde
• 5-Bromo-6-chloro-indan-1-one
• Methyl 5-broMo-6-Methylpicolinate
• 5-BroMo-6-Methylnicotinicacid
• 5-Bromo-6-methyl-nicotinic acid methyl ester
• ETHYL STEARATE