Ammonia → 2-Chloro-6-fluoro-3-nitrobenzaldehyde

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Reaction Steps

Potassium nitrate (638 mg, 6.31 mmol) was dissolved in concentrated sulfuric acid (4.5 mL) and added dropwise to a stirred solution of 2-chloro-6-fluorobenzaldehyde (1.0 g, 6.31 mmol) at room temperature. The mixture was stirred 1 hour at room temperature and then poured into icewater (100 mL) under stirring. The resulting aqueous phase was basified to pH 10 by addition of 25% aqueous ammonia and subsequently extracted with dichloromethane (2×100 mL). The combined organic phases were dried over sodium sulphate, filtered and evaporated to give 2-chloro-6-fluoro-3-nitrobenzaldehyde (196MBT28-A, 1.16 g, 91%). Regioselectivity was confirmed by 13C-NMR.

Provenance & Evidence