Benzimidazole → HCID 60673465, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 1H-benzoimidazole (317 mg, 2.68 mmol) and potassium carbonate (495 mg, 3.58 mmol) in DMF (10 mL) was stirred at 45° C. for 1 h. To the heated suspension was added 2-Bromo-4-bromomethyl-1-methoxy-benzene (500 mg, 1.79 mmol) and the reaction was stirred at 45° C. for 4 h, cooled to room temperature and stirred at room temperature overnight. About half of the solvent was removed under vacuum, and ethyl acetate (30 mL) was added. The organic solution was washed with saturated aqueous ammonium chloride (3×30 mL), water (2×15 mL), and brine (15 mL). The organic extract was dried over anhydrous sodium sulfate and the solvent removed under vacuum to give crude product as an orange oil. The product was purified by flash silica gel column chromatography eluting with 5% methanol in dichloromethane to give the title compound (282.5 mg; 48% yield) and a second crop of 50% pure 2-Bromo-4-bromomethyl-1-methoxy-benzene (207.1 mg).

Provenance & Evidence