2,6-Dichloronitrobenzene

608-31-1

601-88-7

2.1.5. Synthesis of 1,3-dichloro-2-nitrobenzene[4]. 2,6-Dichloroaniline (8.10 g, 50.0 mmol) was dissolved in dichloromethane (200 mL) and the solution was cooled to 0 °C. A solution of 3-chloroperbenzoic acid (24.6 g, 100 mmol) in dichloromethane (250 mL) was slowly added dropwise at 0 °C for a controlled time of 1.5 hours. After the dropwise addition, the reaction mixture was continued to be stirred at room temperature for 2 hours. Subsequently, the reaction mixture was diluted with dichloromethane (250 mL). The reaction mixture was washed sequentially with 2 wt% aqueous sodium thiosulfate (2 x 100 mL), aqueous sodium bicarbonate (4 x 50 mL) and deionized water (200 mL). The organic layer was dried with magnesium sulfate and concentrated under reduced pressure to remove the solvent. The residue was suspended in n-hexane (40 mL), sonicated for 5 min and filtered, and the filter cake was washed with n-hexane (2 x 20 mL) to afford 1,3-dichloro-2-nitrobenzene (6.63 g, 37.7 mmol, 75% yield) as a beige solid.