Diethyl Ether → 1-[(2-Chlorophenyl)methyl]-4,5-dimethyl-1H-imidazole

Participants

Reaction Steps

To a solution of 4.89 g (0.027 mol) of 4,5-dimethylimidazole hydrobromide and 5.7 g (0.028 mol) of 2-chlorobenzyl bromide in 20 ml of DMF is added 6 ml of 50% potassium hydroxide aqueous solution dropwise. The reaction mixture is stirred at room temperature under nitrogen overnight. The reaction mixture is then poured into ether (100 ml)/water (50 ml). The ether layer is separated, washed with water (10 ml×2), dried over anhydrous sodium sulfate and evaporated in vacuo. The raw material is subjected to chromatography on silica gel using dichloromethane-methanol (10:1) as eluant to give 2.67 g (0.012 mol, 44%) of 1-(2-chlorobenzyl)-4,5-dimethylimidazole as a pale yellow oil. LC-MS (M++1): 221.2; 1H-NMR (δ, CDCl3): 2.00 (3H, s), 2.20 (3H, s), 5.07 (2H, s), 6.59 (1H, dd, J=9.2, 2), 7.17 (1H, td, J=8, 1.2), 7.23 (1H, td, J=8, 1.6), 7.38 (2H, dd, J=7.2, 1.6).

Provenance & Evidence