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With N-Bromosuccinimide In dichloromethane at 20℃; for 1 h;
To a solution of 5-chloro- 1H-indazole (2.5 g, 16.1 mmol) in dichloromethane (150 mL) was added N-bromosuccinimide (2.9 g, 16.6 mmol) and the mixture was stirred at room temperature for 1 hour. The mixture was concentrated under reduced pressure and the residue was dissolved in ethyl acetate (100 mL), washed with water (50 mL) and brine (50 mL), dried over sodium sulfate and concentrated under reduced pressure to afford 3-bromo-5-chloro-1H-indazole (3.7 g, 94percent) as a brown solid. ‘H NMR (DMSO-d6, 400 MHz) 13.63 (s, 1H), 7.67 — 7.59 (m, 2H), 7.49 — 7.44 (m, 1H). TLC: 50percent ethyl acetate/heptane (R1: 0.43).
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