4-Bromo-pyridine-2-carboxylic acid ethyl ester Chemical Properties

Melting point:

43 - 44oC

Boiling point:

299.3±20.0 °C(Predicted)

Density 

1.501±0.06 g/cm3(Predicted)

storage temp. 

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

solubility 

Chloroform (Slightly), Methanol (Slightly)

pka

-0.11±0.10(Predicted)

Appearance

White to off-white Solid

4-Bromo-pyridine-2-carboxylic acid ethyl ester Usage And Synthesis

Chemical Properties

Yellow-white solid

Uses

Ethyl 4-Bromopicolinate is a useful compound for the development of inhibitors of murine adipose triglyceride lipase.

Synthesis

1. 1700 g of ethyl pyruvate is slowly added dropwise to 1400 g of a 35% hydrogen peroxide solution at -20°C to -10°C (preferably -10°C). 2. after holding the reaction for 30 minutes, 1400 g of 4-bromopyridine hydrochloride (compound 1) was added to ice water. 3. The pH of the reaction mixture was adjusted to 8-9 using potassium carbonate at a temperature below 10 °C. 4. The reaction mixture was extracted twice with 7 L of dichloromethane (DCM), the organic phases were combined and dried. 5. The dried organic phase was transferred to a 50L reaction flask and 1.4L of water, 4073g of ferrous sulfate heptahydrate and 448mL of concentrated sulfuric acid were added and stirred at room temperature. 6. Under the condition of -10°C to 0°C (preferably -5°C), the pre-prepared ethyl pyruvate/hydrogen peroxide solution was added and the reaction was continued for 4 hours. 7. After completion of the reaction, the reaction mixture was extracted with 7 L of water and the solvent was removed by rotary evaporation to afford 1390 g of ethyl 4-bromopyridine-2-carboxylate (compound 2) in 82% yield.

References

[1] Patent: CN108516953, 2018, A. Location in patent: Paragraph 0067-0071; 0076-0083
[2] Patent: CN105153023, 2018, B. Location in patent: Paragraph 0059; 0060-0061

4-Bromo-pyridine-2-carboxylic acid ethyl ester(62150-47-4)Related Product Information

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