1,2-Dibromoethane → Ethyl 1-(pyridazin-3-yl)cyclopropanecarboxylate

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Reaction Steps

Sodium hydride (60% suspension in mineral oil, 830 mg, 21.66 mmol) was washed with petroleum ether under a nitrogen atmosphere to remove the mineral oil. Dimethylsulfoxide (10 mL) was added and the resulting suspension was stirred for 5 min before adding ethyl 2-(pyridazin-3-yl)acetate (600 mg, 3.61 mmol) and 1,2-dibromoethane (2.03 g, 10.83 mmol) dissolved in dimethylsulfoxide (10 mL) at 10° C. The reaction mixture was allowed to warm to room temperature and stirred for 2 h. The mixture was partitioned between a saturated aqueous solution of ammonium chloride and ethyl acetate. The organics were dried over sodium sulfate and concentrated under reduced pressure. The resulting crude material was purified via column chromatography (100-200 silica gel mesh, 50-60% ethyl acetate in petroleum ether) to afford ethyl 1-(pyridazin-3-yl)cyclopropanecarboxylate (300 mg). MS (ES+APCI) (M+H) 193.0.

Provenance & Evidence