METHYL 3-BROMOMETHYLPYRIDINE-2-CARBOXYLATE Chemical Properties

Boiling point:

338.6±32.0 °C(Predicted)

Density 

1.533±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

0.57±0.10(Predicted)

Appearance

Off-white to brown Solid

METHYL 3-BROMOMETHYLPYRIDINE-2-CARBOXYLATE Usage And Synthesis

Synthesis

General procedure for the synthesis of methyl 3-(bromomethyl)pyridine-2-carboxylate from methyl 3-methylpyridine-2-carboxylate: methyl 3-methylpyridine-2-carboxylate (4.1 g, 27.1 mmol), N-bromosuccinimide (NBS, 5.8 g, 32.5 mmol) and azobisisobutyronitrile (AIBN, 100 mg, 0.61 mmol) were dissolved in carbon tetrachloride (55 mL). The reaction mixture was stirred at 90 °C for 16 h under nitrogen protection. After completion of the reaction, the mixture was filtered and the filtrate was concentrated. The concentrate was purified by column chromatography to afford the target product methyl 3-(bromomethyl)pyridine-2-carboxylate (5.0 g, 80.6% yield). The product was characterized by 1H NMR (400 MHz, CDCl3): δ 8.67 (dd, J = 1.6, 4.6 Hz, 1H), 7.91 (dd, J = 1.5, 7.9 Hz, 1H), 7.48 (dd, J = 4.6, 7.9 Hz, 1H), 4.95 (s, 2H), 4.07-4.03 (m, 3H). lCMS ( m/z): 229.9 ([M + H]+).

References

[1] Patent: WO2015/200677, 2015, A2. Location in patent: Paragraph 00472; 00473
[2] Journal fuer Praktische Chemie (Leipzig), 1987, vol. 329, # 4, p. 557 - 562
[3] Organic Letters, 2017, vol. 19, # 14, p. 3895 - 3898

METHYL 3-BROMOMETHYLPYRIDINE-2-CARBOXYLATE(116986-09-5)Related Product Information

• METHYL-5-BROMOMETHYLPYRIDINE-2-CARBOXYLATE
• METHYL-4-BROMOMETHYLPYRIDINE-2-CARBOXYLATE
• 3-(Bromomethyl)pyridine
• ethyl 3-(bromomethyl)pyridine-2-carboxylate
• METHYL 3-BROMOMETHYLPYRIDINE-2-CARBOXYLATE