Dimethyl Sulfate → 6-broMo-1-Methyl-1H-benzo[d]iMidazol-2(3H)-one

Participants

Reaction Steps

tert-Butyl 5-bromo-2-oxo-2,3-dihydrobenzo[d]imidazole-1-carboxylate (12 g, 38 mmol) (Puwen Zhang, et. al., Bioorganic & Medicinal Chemistry Letters 11 (2001) 2747-2750 hereby incorporated by reference) and anhydrous disodium carbonate (3.2 mL, 77 mmol) were mixed in 200 mL THF. To this mixture was added dimethyl sulfate (15 mL, 153 mmol). The mixture was stirred at room temperature for 18 hours. The solvent was evaporated. The residue was dissolved in EtOAc and washed with brine and dried over sodium sulfate. The solvent was evaporated. The residue was taken up in MeOH (50 mL) and allowed to stand 18 hours. The solvent was evaporated, and the residue was triturated from MeOH (25 mL) to provide the product as a white solid (8.7 g, 100%). LCMS (API-ES) m/z: 227, 229 (M+H+).

Provenance & Evidence