28898-02-4

348-54-9

1493-27-2

28898-02-4

GENERAL METHOD: Suspend NaH (75 mmol) in DMF (60 mL) at 0°C and slowly add o-fluoroaniline (50 mmol). After maintaining 0°C and stirring for 30 min, a solution of 1-fluoro-2-nitrobenzene (60 mmol) in DMF (30 mL) was added dropwise. The reaction mixture was gradually warmed to room temperature and stirred continuously for 16 hours. Upon completion of the reaction, the mixture was carefully poured into stirred saturated NH4Cl solution (500 mL) to quench the reaction. The precipitate was collected by filtration, the filter cake was washed with water and finally purified by recrystallization from methanol to afford the target product 2-fluoro-N-(2-nitrophenyl)aniline (15j). The product was a red solid with a yield of 74.1% and a melting point of 74.4-75.8 °C. 1H NMR (400 MHz, DMSO-d6) δ 9.28 (s, 1H), 8.14 (d, J = 8.0 Hz, 1H), 7.51 (m, 2H), 7.35 (m, 3H), 6.90 (m, 2H); MS (ESI) m/z (%). 231.1 [M-H]-.