p-Fluoronitrobenzene → HCID 20282214, compound

Participants

Reaction Steps

A solution of 1-(3,3-dimethyl-2-hydroxy-n-butyl)imidazole (5.2 g) in a mixture of 50 ml of dimethylformamide and 25 ml of toluene was treated with sodium hydride (3.4 g of 50% dispersion in mineral oil) and stirred at room temperature. After the evolution of hydrogen ceases, manganese dioxide (3.0 g) was added and the mixture cooled in an ice bath. To this mixture was added p-fluoronitrobenzene (8.0 g) and the resulting mixture stirred at room temperature for 3 hours. The reaction mixture was then filtered through Celite washing the residue with toluene, and the filtrate washed several times with water. The toluene layer was separated and dried over sodium sulfate, and evaporated to give yellow crystals. After trituration with ether, the resulting solid was chromatographed on silica gel eluting with 5% methanol in methylene chloride. The resulting product was recrystallized from ethyl acetate to give 6.5 g of 1-[2-(4-nitrophenoxy)-3,3-dimethyl-n-butyl]imidazole.

Provenance & Evidence