Dimethylformamide → 5-Bromo-2-(2,2,2-trifluoroethoxy)pyridine

Participants

Reaction Conditions

Reaction Steps

2,2,2-Trifluoroethanol (6.15 mL, 84.4 mmol) was placed into a flask with DMF (141 mL). To the reaction mixture was added NaH (3.4 g, 84.4 mmol) in portions. The reaction was then stirred for 30 min at 25° C. At this point, 2,5-dibromopyridine was added and the mixture was heated to 90° C. and stirred at that temperature overnight. The reaction was cooled to rt and diluted with EtOAc (100 mL). The organic layer was washed with H2O (3×150 mL), brine (2×100 mL), dried (MgSO4), filtered, and concentrated. This material was purified by column chromatography (15:1 hexane:EtOAc) to give 5-bromo-2-(2,2,2-trifluoroethoxy)pyridine as an oil.

Provenance & Evidence