2-FLUOROPYRIDINE-3-BORONIC ACID PINACOL ESTER Chemical Properties

Melting point:

42-45°C

Boiling point:

309.9±27.0 °C(Predicted)

Density 

1.09±0.1 g/cm3(Predicted)

storage temp. 

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

form 

solid

pka

-0.44±0.12(Predicted)

color 

yellow

Safety Information

Risk Statements 

36/37/38

Safety Statements 

26-37

TSCA 

No

HazardClass 

IRRITANT

HS Code 

29319090

2-FLUOROPYRIDINE-3-BORONIC ACID PINACOL ESTER Usage And Synthesis

Chemical Properties

White to light yellow solid

Uses

2-Fluoropyridine-3-boronic acid, pinacol ester

Synthesis

Freshly distilled diisopropylamine (42.5 g, 0.42 mol) was dissolved in ether under nitrogen protection and cooled to 0°C. n-Butyllithium (2.5 M, 175 mL) was slowly added and stirred continuously at 0 °C for 30 min. Subsequently, the reaction system was cooled to -60 °C and an ether solution of 2-fluoropyridine (34.0 g, 0.35 mol) was added slowly dropwise and stirring was continued at -60 °C for 1 hour. An ether solution of triisopropoxyborate (82.4 g, 0.44 mol) was added dropwise, then the mixture was gradually warmed to room temperature and stirred for 2 hours. An ether solution of pinacol (55.6 g, 0.47 mol) was added dropwise over 10 minutes, followed by glacial acetic acid (22.1 g, 0.37 mol). The reaction mixture was stirred overnight at room temperature, filtered and the filtrate was extracted with 5% aqueous sodium hydroxide solution. The pH of the aqueous phase was slowly adjusted to 6-7 with 3N hydrochloric acid, ensuring that the temperature was below 5 °C, and then extracted with ethyl acetate. The organic phases were combined and concentrated in vacuum to remove the solvent to afford the target product 2-fluoropyridine-3-boronic acid pinacol ester (27.0 g, 34% yield).

References

[1] Patent: CN103102349, 2017, B. Location in patent: Paragraph 0171-0173

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