| Identification | Back Directory | [Name]
4-Bromo-pyridine-2-carboxylic acid ethyl ester | [CAS]
62150-47-4 | [Synonyms]
ethyl 4-broMopicolinate
Ethyl 4-bromopyridine-2-carboxylate
4-Bromo-pyridine-2-carboxylic acid ethyl ester
2-Pyridinecarboxylic acid, 4-broMo-, ethyl ester
4-Bromo-pyridine-2-carboxylic acid ethyl ester ISO 9001：2015 REACH | [Molecular Formula]
C8H8BrNO2 | [MDL Number]
MFCD09839150 | [MOL File]
62150-47-4.mol | [Molecular Weight]
230.06 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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 |
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