5-BROMO-2-CHLORO-4-(TRIFLUOROMETHYL)PYRIDINE Chemical Properties

Melting point:

11-13 °C

Boiling point:

80-81 °C(Press: 16 Torr)

Density 

1.813 g/cm3

storage temp. 

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

form 

liquid

pka

-3.73±0.10(Predicted)

color 

Clear, yellow

Safety Information

Hazard Codes 

Xi

HazardClass 

IRRITANT

HS Code 

2933399990

5-BROMO-2-CHLORO-4-(TRIFLUOROMETHYL)PYRIDINE Usage And Synthesis

Uses

5-Bromo-2-chloro-4-(trifluoromethyl)pyridine is an organic compound mainly used as a pharmaceutical intermediate, especially for the synthesis of certain drugs.

Synthesis

To a stirred solution of 5-bromo-2-chloro-4-iodopyridine (20.0 g, 63.09 mmol, 1.0 eq.) in N,N-dimethylformamide (DMF, 200 mL) at room temperature and under argon protection was added sequentially methyl 2,2-difluoro-2-(fluorosulfonyl)acetate (16.15 mL, 126.18 mmol, 2.0 eq.) and iodide cuprous iodide (CuI, 24.02 g, 126.18 mmol, 2.0 equiv). The reaction mixture was heated to 100 °C with continuous stirring for 6 hours. The reaction progress was monitored by thin layer chromatography (TLC) and non-polar spots were observed. After completion of the reaction, the mixture was diluted with water (200 mL), filtered and washed sequentially with n-pentane (1 L) and cold water (3 L). The organic layer was separated and dried over anhydrous sodium sulfate and subsequently concentrated under reduced pressure at 30 °C. The crude product was purified by silica gel column chromatography (100-200 mesh) with petroleum ether solution of 5% ethyl acetate as eluent to afford the target product 5-bromo-2-chloro-4-trifluoromethylpyridine (9.0 g, yield 55.2%) as a liquid compound.TLC conditions: petroleum ether solution of 5% ethyl acetate; Rf value: 0.7.

References

[1] Patent: WO2017/147700, 2017, A1. Location in patent: Paragraph 00355
[2] Patent: WO2017/147701, 2017, A1. Location in patent: Paragraph 00320; 00322-00323

5-BROMO-2-CHLORO-4-(TRIFLUOROMETHYL)PYRIDINE(823221-93-8)Related Product Information

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