Thionyl Chloride → 2-(Chloromethyl)-1-methylbenzimidazole

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A solution of 2-hydroxymethyl-1-methylbenzimidazole (1.1 g, 6.7 mmol) in thionyl chloride (10 ml) was stirred at ambient temperature for 15 minutes and then heated at reflux for 15 minutes. The volatiles were removed by evaporation and the residue purified by column chromatography eluting with methylene chloride/methanol (95/5) to give 2-chloromethyl-1-methylbenzimidazole (506 mg, 36%). 1H NMR Spectrum: (DMSOd6; CF3COOD) 4.07(s, 3H); 5.38(s, 2H); 7.6-7.7(m, 2H); 7.9(d, 1H); 8.05(dd, 1H) MS-ESI: 181 [MH]+

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