Dimethylformamide → 5-(4-bromophenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazole

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To a solution of 5-(4-bromophenyl)-1H-1,2,4-triazole (5.40 g, 24.1 mmol) in DMF (48.2 mL, 24.1 mmol) at 0° C. was carefully added NaH (1.16 g, 28.9 mmol). The resultant mixture was stirred for 30 minutes prior to the addition of (2-(chloromethoxy)ethyl)trimethylsilane (6.38 mL, 36.2 mmol). The reaction mixture was stirred 0° C. for 15 minutes before removal of the ice bath and the mixture was allowed to warm to ambient temperature stirring for 2 hours. The reaction mixture was diluted with H2O (150 mL) and extracted with EtOAc (2×200 mL). The combined organic extracts were washed with brine, dried (Na2SO4), filtered and concentrated to provide 10.09 g as a pale yellow oil which solidified upon standing. Purification by normal phase chromatography on silica eluting with 0-50% EtOAc/Hexanes provided 3-(4-bromophenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazole and 5-(4-bromophenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazole (7.94 g, 93%) as a mixture of two regioisomers. LCMS (APCI+) m/z 354, 356 [M+H]+.

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