3-Chlorobenzaldehyde → 5-Chloro-2-nitrobenzaldehyde

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Reaction Steps

3-Chlorobenzaldehyde (15 g, 107 mmol) was added to concentrated sulfuric acid (150 mL) at −20° C., followed by addition of potassium nitrate (11.9 g, 117 mmol) in portions, keeping the temperature below −10° C. After addition, the mixture was stirred for 30 minutes and then poured into ice-water. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined, washed by brine, dried over anhydrous sodium sulfate, evaporated and purified by silica gel chromatography to afford the product 5-chloro-2-nitrobenzaldehyde (12.0 g, yield 60.6%).

Provenance & Evidence