3-Bromo-2,6-difluoropyridine synthesis
- Product Name:3-Bromo-2,6-difluoropyridine
- CAS Number:80392-79-6
- Molecular formula:C5H2BrF2N
- Molecular Weight:193.98
866755-20-6
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80392-79-6
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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
1513-65-1
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54903-86-5
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80392-79-6
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685517-67-3
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80392-79-6
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141-86-6
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80392-79-6
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