Synthesis
The general procedure for the synthesis of N-ethyl-4-fluoroaniline from triethylamine and 4-fluoroaniline is as follows: first, a mixed solution of IrCl3 (2 mol%, 0.02 mmol), ligand L1 (2.4 mol%, 0.024 mmol), sodium hydroxide (0.20 mmol), and xylene (3 mL) was stirred for 1 hr at room temperature in a Schlenk tube . Subsequently, 4-fluoroaniline (1.00 mmol), triethylamine (1.0 mL) and sodium hydroxide (1.00 mmol) were added to the reaction system. The reaction mixture was heated at 150 °C for 20 h, after which it was cooled to room temperature. Upon completion of the reaction, the resulting solution was purified directly by column chromatography using petroleum ether/ethyl acetate (10:1) as eluent to give the final target product N-ethyl-4-fluoroaniline (3a).
References
[1] ACS Catalysis, 2014, vol. 4, # 11, p. 3910 - 3918
[2] Tetrahedron Letters, 2016, vol. 57, # 41, p. 4588 - 4591
