3-Bromo-2,6-difluoropyridine Chemical Properties

Boiling point:

180.9±35.0 °C(Predicted)

Density 

1.808±0.06 g/cm3(Predicted)

storage temp. 

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

pka

-8.45±0.10(Predicted)

form 

liquid

color 

Yellow

InChI

InChI=1S/C5H2BrF2N/c6-3-1-2-4(7)9-5(3)8/h1-2H

InChIKey

GLWVPTDEVHPILQ-UHFFFAOYSA-N

SMILES

C1(F)=NC(F)=CC=C1Br

Safety Information

HS Code 

2933399990

3-Bromo-2,6-difluoropyridine Usage And Synthesis

Uses

3-Bromo-2,6-difluoropyridine is mainly used as an intermediate in organic synthesis, especially in medicinal chemistry for the synthesis of biologically active compounds.

Synthesis

GENERAL METHOD: To a solution of 2,6-dichloro-3-bromopyridine (4.70 g, 20.7 mmol) in dimethyl sulfoxide (DMSO, 103 mL) was added cesium fluoride (12.6 g, 82.9 mmol) at room temperature. The reaction mixture was stirred in air at 80 °C for 8 hours. After completion of the reaction, the mixture was poured into room temperature water and extracted with ether (Et2O). The organic layer was separated, washed sequentially with water and saturated saline, dried over anhydrous sodium sulfate (Na2SO4) and subsequently concentrated under reduced pressure (400 Torr, 40°C). Purification of the residue by column chromatography (silica gel, hexane solution of ethyl acetate as eluent) afforded 3-bromo-2,6-difluoropyridine (2.58 g, 64% yield) as a colorless oil.1H NMR (CDCl3) δ: 6.79 (1H, dd, J = 8.3, 3.0 Hz), 8.03 (1H, ddd, J = 8.4, 8.4, 7.0 Hz).19F NMR (CDCl3) δ: -69.3 Hz, -63.8 Hz.Compounds 4B-8B were prepared according to the method similar to 3B.

References

[1] Tetrahedron Letters, 2015, vol. 56, # 44, p. 6043 - 6046

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