Water → 9,9-Dibutyl-2-nitro-9H-fluorene

Participants

Reaction Conditions

Reaction Steps

12.66 g of 2-nitrofluorene (1) (60 mmol), 21.0 g of potassium hydroxide (0.3 mol, purity: 80%), and 1.01 g of potassium iodide (6 mmol) were dissolved in 200 ml of anhydrous dimethylsulfoxide under nitrogen atmosphere, and a reaction temperature was maintained at 15° C. Then, 33 ml of n-bromobutane (0.3 mol) was slowly added thereto for 2 hours, followed by stirring at 15° C. for 1 hour. Thereafter, 200 ml of distilled water was added to the reaction mixture and stirred for about 30 minutes, a product was extracted with 300 ml of dichloromethane, and the extracted organic layer was washed with 100 ml of distilled water three times. Then, the recovered organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled under reduced pressure. The obtained product was purified using a silica gel column chromatography (eluent: dichloromethane:n-hexane=20:1), thereby obtaining 15.4 g of 9,9-di-n-butyl-2-nitrofluorene (5) (79.5%) as a light yellow product.

Provenance & Evidence