ChemicalBook CAS DataBase List 3-Bromo-2-fluoropyridine

3-Bromo-2-fluoropyridine synthesis

8synthesis methods

Product Name:3-Bromo-2-fluoropyridine
CAS Number:36178-05-9
Molecular formula:C5H3BrFN
Molecular Weight:175.99

52200-48-3

36178-05-9

GENERAL METHOD: 2,3-Dichloropyridine (1.00 g, 6.76 mmol) was dissolved in DMSO (33.8 mL) at room temperature, followed by the addition of CsF (2.053 g, 13.51 mmol). The reaction mixture was stirred at 110 °C for 20 h in air. Upon completion of the reaction, the reaction mixture was quenched with ice water and extracted with EtOAc. The organic layer was separated, washed sequentially with water and brine, dried over anhydrous Na2SO4 and subsequently concentrated under reduced pressure. Purification of the residue by column chromatography (silica gel as stationary phase and EtOAc in hexane as eluent) afforded 3-chloro-2-fluoropyridine (0.639 g, 4.86 mmol, 71.9% yield) as a colorless oil. Compounds 3B'-8B' were prepared by a method similar to the synthetic procedure described above for 2B'.

52200-48-3
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$11.00/1g

36178-05-9
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$15.00/5g

Yield:36178-05-9 73%

Reaction Conditions:

with cesium fluoride in dimethyl sulfoxide at 130; for 4 h;

Steps:

3-Bromo-2-fluoropyridine(3B')
General procedure: To a solution of 2,3-dichloropyridine(1.00 g, 6.76 mmol) in DMSO (33.8 ml) was added CsF (2.053 g, 13.51mmol) at room temperature. The mixture was stirred at 110 °C under air for 20h. The mixture was quenched with water at room temperature and extracted withEtOAc. The organic layer was separated, washed with water and brine, dried overNa₂SO₄ and concentrated in vacuo. The residue waspurified by column chromatography (silica gel, eluted with EtOAc in hexane) togive 3-chloro-2-fluoropyridine (0.639 g, 4.86 mmol, 71.9 %) as colorlessoil. Thecompound 3B'-8B' were prepared in amanner similar to that described for 2B'.

References:

Katoh, Taisuke;Tomata, Yoshihide;Tsukamoto, Tetsuya;Nakada, Yoshihisa [Tetrahedron Letters,2015,vol. 56,# 44,p. 6043 - 6046] Location in patent:supporting information

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372-48-5 Synthesis