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About:
5-bromo-3-fluoropyridine is an organic intermediate that can be prepared from 3, 5-dibromo-pyridine by a one-step reaction with NFSI, or from 5-bromo-nicotinamide by a two-step reaction.
Preparation:
Under nitrogen, 3, 5-dibromopyridine (1.21g) was added to a 50mLSchlenk flask containing THF (5.0mL). At 0°C, i-PrMgCl·LiCl (5.5mmol) of THF (1.16M, 4.7mL) was added to the flask. Stir the reaction mixture at 0°C for 1 hour. Vacuum removal of solvent (0.5mbar, 40°C, 0.5 hours). CH2Cl2 (5mL) was added to the reaction mixture and NFSI (1.89g, 6mmol) in CH2Cl2 (15mL) and perfluoronaphthalane (5mL) was slowly added to the reaction mixture at -78°C. Stir the reaction mixture at 0°C for 30 minutes. The reaction mixture was stirred at 25°C for 2 hours, then poured into a cold saturated NH4Cl aqueous solution (50mL), extracted with CH2Cl2 (3×50mL), and dried with Na2SO4. The organic layer was filtered, the organic layer was concentrated under vacuum, the crude residue was purified by column chromatography (SiO2) using pentane /Et2O (20:1) as eluent to obtain 5-bromo-3-fluoropyridine.
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