ChemicalBook CAS DataBase List 3-Chloro-2-fluoro-pyridine

3-Chloro-2-fluoro-pyridine synthesis

4synthesis methods

Product Name:3-Chloro-2-fluoro-pyridine
CAS Number:1480-64-4
Molecular formula:C5H3ClFN
Molecular Weight:131.54

2402-77-9

1480-64-4

GENERAL METHOD: To a solution of 2,3-dichloropyridine (1.00 g, 6.76 mmol) in dimethyl sulfoxide (DMSO, 33.8 mL) was added cesium fluoride (CsF, 2.053 g, 13.51 mmol) at room temperature. The reaction mixture was stirred in air at 110 °C for 20 hours. After completion of the reaction, the reaction mixture was quenched with ice water and extracted with ethyl acetate (EtOAc). The organic layer was separated, washed sequentially with water and saturated brine, dried over anhydrous sodium sulfate (Na2SO4) and concentrated under reduced pressure. The residue was purified by silica gel column chromatography using ethyl acetate (EtOAc) in hexane as eluent to afford 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 for compound 2B'.

2402-77-9 Synthesis

2402-77-9
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1480-64-4
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Yield:1480-64-4 71.9%

Reaction Conditions:

with caesium fluoride in (methylsulfinyl)methane at 110; for 20 h;

Steps:

3-Chloro-2-fluoropyridine(2B')

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

372-48-5 Synthesis