Chlorosuccinimide → 2,3,4-Trichloro-6-nitrobenzenamine

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Reaction Conditions

Reaction Steps

4,5-Dichloro-2-nitroaniline (15.2 g, 73.2 mmol), N-chlorosuccinimide (12.2 g, 91.6 mmol) and N,N-dimethylformamide (150 mL) were combined and the resulting orange solution was heated to 100° C. for 1 h. The solution was allowed to cool to room temperature and was poured into a flask containing ice water (1.2 L). The yellow solid was collected and was dissolved in dichloromethane (1.5 L), resulting in two-phases. The organic layer was collected and was dried over magnesium sulfate, filtered and the solvents were removed under reduced pressure by rotary evaporation to leave 17.6 g (98%) of a yellow solid. MS (Cl): m/z 239.

Provenance & Evidence