Hydrogen Peroxide → 1,3-Dichloro-2-nitrobenzene

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0.66 g (2.64 mmol) of tungstic acid and 0.40 g (1.23 mmol) of tetrabutylammonium bromide were added to a suspension of 2.0 g (12.3 mmol) of 2,6-dichloroaniline in 6 ml of water, and the mixture was heated to 40° C. 4.9 g (43.1 mmol) of a 30% hydrogen peroxide solution was added. The pH value at this time was 1.5. Then, the mixture was stirred at 40° C. for 16 hours. After the disappearance of the 2,6-dichloroaniline was confirmed by gas chromatography (area percentage method), 3 ml of methanol and 3.49 g (30.8 mmol) of a 30% hydrogen peroxide solution were added, and 2.8 g (12.3 mmol) of a 25% aqueous potassium hydroxide solution was added dropwise while the temperature of the reaction liquid was adjusted to 40° C. or less. After the completion of the dropwise addition, the mixture was stirred at room temperature overnight, and the reaction was completed. After the completion of the reaction, 30 ml of toluene and 20 ml of water were added, and the mixture was stirred for a while, and filtered. The filtrate was separated. The obtained organic phase was washed with 10 ml of water, and then heated to reflux, and dehydrated. Thus, a toluene solution of 2,6-dichloronitrobenzene was obtained. This solution was analyzed by gas chromatography by the absolute calibration method, and as a result, the yield was 80%. The amount of the potassium hydroxide added is sufficient to make the pH condition alkaline.

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