METHYL-5-BROMOMETHYLPYRIDINE-2-CARBOXYLATE Chemical Properties

Boiling point:

334℃

Density 

1.533

Flash point:

156℃

storage temp. 

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

pka

0.78±0.10(Predicted)

Appearance

White to off-white Solid

METHYL-5-BROMOMETHYLPYRIDINE-2-CARBOXYLATE Usage And Synthesis

Synthesis

General procedure for the synthesis of 5-bromomethylpyridine-2-carboxylic acid methyl ester from 5-methylpyridine-2-carboxylic acid: in a 500 mL round bottom flask, N-bromosuccinimide (NBS, 14.13 g, 79.38 mmol, 1.20 eq.) and azobisisobutyronitrile (AIBN, 217 mg, 1.32 mmol, 0.02 eq.) were added to a 5- methyl pyridine-2-carboxylate (10 g, 66.15 mmol, 1.00 equiv) in a solution of carbon tetrachloride (CCl4, 200 mL). The reaction mixture was stirred at 80 °C for 16 hours. After completion of the reaction, the mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography using ethyl acetate/petroleum ether (5% to 25% gradient) as eluent to afford methyl 5-bromomethylpyridine-2-carboxylate (9.6 g, 57% yield) as a yellow solid. Mass spectrum (MS): m/z = 229.9 [M + H]+.

References

[1] Patent: US2016/96834, 2016, A1. Location in patent: Paragraph 0328
[2] Patent: WO2007/22371, 2007, A2. Location in patent: Page/Page column 90
[3] Patent: WO2012/80221, 2012, A1. Location in patent: Page/Page column 84
[4] Patent: US2013/274260, 2013, A1. Location in patent: Paragraph 0622-0623
[5] Patent: WO2013/3505, 2013, A1. Location in patent: Page/Page column 58

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