Ethyl Acetate → 5-Fluoro-2-{[(2E)-3-phenylprop-2-enyl]oxy}aniline

Participants

Reaction Conditions

Reaction Steps

4-Fluoro-2-nitrophenyl (2E)-3-phenylprop-2-enyl ether (5-1, 20.2 g, 73.9 mmol) was dissolved in MeOH (300 mL) and treated with NH4Cl (20.5 g, 370 mmol) and Zn powder (24.2 g, 370 mmol) in small portions to prevent temperature from exceeding 50° C. during the addition. The suspension was vigorously stirred at 25° C. and then at 60° C. until completion as monitored by TLC and LC/MS. Upon completion, EtOAc was added (900 mL) and the reaction was filtered through celite and concentrated. The product was recrystallized from EtOAc/hexanes after a filtration to remove insoluble NH4Cl, and pure 5-fluoro-2-{[(2E)-3-phenylprop-2-enyl]oxy}aniline (5-2) was isolated as a brown solid. 1H NMR (300 MHz, CDCl3) δ 7.38 (m, 5H), 6.74 (dd, J=8.8, 4.9 Hz, 1H), 6.72 (d, J=17.4 Hz, 1H), 6.47 (dd, J=9.7, 3.1 Hz, 1H), 6.42 (m, 2H), 4.67 (dd, J=5.9, 1.3 Hz, 2H), 3.22 (br s, 2H); MS (M+H+, C15H14FNO) 244.2 found 244.3 required.

Provenance & Evidence