2,4,5-Tribromoimidazole → 2,4,5-tribromo-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-Imidazole

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Reaction Steps

To a solution of 2,4,5-tribromo-1H-imidazole (10.3 g, 32 8 mmol) in anhydrous N,N-dimethylformamide (100 ml) is slowly added NaH (1.4 g, 36.1 mmol, 60% in mineral oil) at room temperature. The suspension is stirred for 15 minutes and 2-(Trimethylsilyl)ethoxymethyl chloride (5.8 ml, 32.8 mmol) is added. The mixture is stirred at room temperature for 3 hours. The reaction mixture is diluted with water (250 ml) and extracted with ethyl acetate (3×50 ml). The combined organic layer is washed with water (50 ml), brine, dried over MgSO4, filtered, and concentrated in vacuo to yield 2,4,5-tribromo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole as a yellow waxy solid 13.8 g, 97%.

Provenance & Evidence