Benzyl Bromide → 2-Benzyl-4,5-dichloro-2,3-dihydropyridazin-3-one

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Reaction Steps

A stirred mixture of 4,5-dichloropyridazin-3(2H)-one (26.7 g, 160 mmol), benzyl bromide (19.3 mL, 160 mmol), tetrabutylammonium bromide (2.61 g, 8.10 mmol), and potassium carbonate (56.0 g, 405 mmol) in acetonitrile (405 mL) was heated to reflux for 2 h. The mixture was cooled to room temperature, filtered through a fitted glass, concentrated, and purified by flash chromatography to afford the title compound as a white solid. 1H NMR (500 MHz, CD3SOCD3) δ 8.23 (s, 1H); 7.27-7.35 (m, 5H); 5.27 (s, 2H). LRMS (APCI) calc'd for (C11H9Cl2N2O) [M÷H]+, 255.0. found 255.0.

Provenance & Evidence