2-(Trifluoromethyl)pyridine

Uses

Synthesis Reference(s)

Synthesis

109-04-6

81290-20-2

368-48-9

AgF (1.27 g, 10 mmol) was dissolved in 10 mL of DMF at room temperature and stirred thoroughly. Subsequently, Me3SiCF3 (1.7 g, 12 mmol) was added to the mixture and stirring was continued for 20 minutes. Next, copper powder (1.0 g, 15 mmol) was added and the reaction mixture was stirred for 4 hours to ensure complete formation of CuCF3. Then, the corresponding halogenated compound (9 mmol, 4.5 mmol for 2,6-dibromopyridine) was added and the reaction mixture continued to be stirred under the conditions listed in Table 1. The progress of the reaction was monitored by 19F NMR spectroscopy until the signal of CuCF3 completely disappeared and the reaction was terminated. Upon completion of the reaction, the mixture was filtered to remove the solid precipitate and the filtrate was poured into 50 mL of water. The organic layer in the aqueous phase was extracted with ether and the extract was dried with MgSO4. Finally, the ether was removed by evaporation and the residue was purified by distillation under reduced pressure or crystallization to give the target product 2-trifluoromethylpyridine.

References