2-Amino-5-fluorobenzotrifluoride

2314-97-8

371-40-4

393-39-5

General procedure for the synthesis of 2-amino-5-fluorobenzotrifluoride from trifluoroiodomethane and 4-fluoroaniline: a 25 mL Schlenk tube was filled with a magnetic stirring bar, and 4-fluoroaniline (1.2 mmol, 3.0 eq.) or heterocyclic amine (0.8 mmol, 2.0 eq.), potassium carbonate (K2CO3, 0.8 mmol, 2.0 eq.) and fac- Ir(ppy)3 (2.6 mg, 0.004 mmol, 1 mol%). The reaction vessel was evacuated and displaced three times with argon (Ar), then trifluoroiodomethane (CF3I) stock solution (0.56 mL, 0.71 mmol/mL in 1,2-dichloroethane or 0.36 mL, 1.11 mmol/mL, 1.0 equiv in DMSO) and anhydrous 1,2-dichloroethane (3 mL) were added. The cap of the tube was screwed on tightly and the reaction was stirred for 24 h at room temperature under the illumination of a blue LED (12 W). Upon completion of the reaction, the reaction mixture was filtered through a diatomaceous earth pad and washed with ethyl acetate (3 x 5 mL). The filtrate was concentrated and the residue was purified by silica gel column chromatography to afford the target product 2-amino-5-fluorobenzotrifluoride.