52301-88-9

13324-11-3

52301-88-9

General procedure for the synthesis of 2-chloro-4-nitrobenzyl alcohol from methyl 2-chloro-4-nitrobenzoate: In a 250 mL round-bottom flask, methyl 2-chloro-4-nitrobenzoate (5 g, 23 mmol) was dissolved in anhydrous dichloromethane (100 mL). The reaction system was cooled to -78 °C under nitrogen protection. Bis(2-methylpropyl)alumina (35 mL, 35 mmol, 1 M solution in hexane) was added slowly and dropwise. The reaction mixture was kept stirred at -78 °C for 4 h. The reaction was subsequently quenched by the addition of water (5 mL). The reaction mixture was gradually warmed to room temperature over 20 min. Anhydrous sodium sulfate (15 g) was added to dry it. after 10 min, the desiccant was removed by filtration. The filtrate was concentrated under reduced pressure to give 2-chloro-4-nitrobenzyl alcohol in 95% yield.