Potassium Hydroxide → 1-(2-(allyloxy)-4-nitrophenyl)-4-chloro-1H-imidazole

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-chloro-1H-imidazole (3.31 g, 32.0 mmol), 2-(allyloxy)-1-chloro-4-nitrobenzene (6.50 g, 30.8 mmol), and potassium hydroxide flakes (1.90 g, 33.9 mmol) in anhydrous DMSO (50 mL) was heated at 90° C. for 20 h under nitrogen. The reaction mixture was allowed to cool to rt and ice-cold water was added. The resulting precipitate was collected by vacuum filtration. The product was dried, and purified by column chromatography (5% EtOAc/Hexane) to afford the yellow solid 1-(2-(allyloxy)-4-nitrophenyl)-4-chloro-1H-imidazole (3.48 g, 40% yield). LC-MS (M+H)+280.2. 1H NMR (400 MHz, CDCl3) δ ppm 7.97-7.93 (2H, m), 7.77 (1H, s), 7.44 (1H, d, J=8.8 Hz), 6.05-5.98 (1H, m), 5.45-5.37 (2H, m), 4.70-4.65 (2H, m).

Provenance & Evidence