Water → 1-Amino-2-bromonaphthalene

Beteiligte Stoffe

Reaktionsschritte

To a solution of naphthalen-1-amine (10 g, 69.8 mmol) in N,N-dimethylformamide (50 mL) at 0° C. was added N-bromosuccinimide (12.4 g, 69.8 mmol) in N,N-dimethylformamide (50 mL). The reaction mixture stirred for 1 hour before the addition of water (400 mL). The product was extracted with ethyl acetate (3×200 mL), and the combined ethyl acetate washes were extracted with brine (3×50 mL). The ethyl acetate was concentrated, and the crude material was purified by flash chromatography (0-20% ethyl acetate/hexanes) to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.15-8.24 (m, 1H) 7.73-7.82 (m, 1H) 7.40-7.52 (m, 3H) 7.07 (d, J=8.82 Hz, 1H) 5.87 (s, 2H); MS (APCI+) m/z 222.0 (M+H)+.

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