ChemicalBook CAS DataBase List 3-Bromo-2,6-difluoropyridine

3-Bromo-2,6-difluoropyridine synthesis

5synthesis methods

Product Name:3-Bromo-2,6-difluoropyridine
CAS Number:80392-79-6
Molecular formula:C5H2BrF2N
Molecular Weight:193.98

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Yield: 64%

Reaction Conditions:

with cesium fluoride in dimethyl sulfoxide at 80; for 8 h;

Steps:

3-Bromo-2,6-difluoropyridine(3B)
General procedure: To asolution of 3-bromo-2,6-dichloropyridine (4.70 g, 20.7 mmol) in DMSO (103 ml)was added cesium fluoride (12.6 g, 82.9 mmol) at room temperature. The mixturewas stirred at 80 °C under air for 8 h. The mixture was poured into water atroom temperature and extracted with Et₂O. The organic layer wasseparated, washed with water and brine, dried over Na₂SO₄and concentrated in vacuo. (400 Torr, 40 °C). The residue was purified bycolumn chromatography (silica gel, eluted with EtOAc in hexane) to give 3-bromo-2,6-difluoropyridine (3B) (2.58 g, 64%) as 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. The compound 4B-8B were prepared in a manner similarto that described for 3B.

References:

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