Isoamyl Nitrite → 4-Bromo-6-chloro-3-(2,2,2-trifluoro-ethoxy)-pyridazine

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Reaction Steps

To a suspension of 2.30 g 6-chloro-3-(2,2,2-trifluoro-ethoxy)-pyridazin-4-ylamine in 23 mL dibromomethane was added 5.11 g isoamylnitrite at once and drop wise 4.642 g trimethylbromosilane at ambient temperature (during ca 10 min). A moderate exotherm was observed and a dark brown solution was obtained. The mixture was stirred at ambient temperature for 18 h. The solvents were evaporated and the residue was purified (3×) by chromatography on silica gel using a gradient of heptane to dichloromethane to yield 0.70 g of the title compound as white crystalline solid, MS 292 (M+H)+.

Provenance & Evidence