Aniline → (3-Chloro-2-nitrophenyl)phenylamine

Beteiligte Stoffe

Reaktionsschritte

LiHMDS (1.0M in THF, 23 mL) was added to a stirred solution of phenylamine (1.12 g, 12.0 mmol) in THF (15 mL) at −78° C. under a nitrogen atmosphere. Stirring was continued for 30 min then 1-chloro-3-fluoro-2-nitrobenzene (1.92 g, 10.9 mmol) in THF (15 mL) was added. The reaction mixture was stirred at −78° C. for 30 min, then slowly warmed to RT and stirred at RT for 2 h. The reaction mixture was poured into a saturated solution of NH4Cl and then extracted with EtOAc (×2). The combined organic layers were washed with brine, then dried (Na2SO4) and concentrated in vacuo affording (3-Chloro-2-nitrophenyl)phenylamine as a dark brown oil (2.85 g, quantitative). 1H NMR (CDCl3, 400 MHz): δ 7.41-7.25 (3H, m), 7.23-7.12 (5H, m), 6.96-6.91 (1H, m).

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