Phosphorus oxychloride → 6-Bromo-4-chloro-3-nitroquinoline

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Reaction Steps

20 g (74.3 mmol) of 6-bromo-3-nitro-quinolin-4-ol (Example 1b) in 150 ml (1.63 mol) of POCl3 are stirred for 45 min at 120° C. The mixture is cooled to rt and poured slowly into ice-water. The precipitate is filtered off, washed with ice-cold water, and dissolved in CH2Cl2. The organic phase is washed with cold brine, and the aqueous phase is discarded. After drying over MgSO4, the organic solvent is evaporated to dryness to provide the title compound. 1H NMR (CDCl3): δ 9.20/s (1H), 8.54/d (1H), 8.04/d (1H), 7.96/dd (1H); analytical HPLC: tret=4.32 min (Grad 1).

Provenance & Evidence