1722-10-7

The Journal of Organic Chemistry, 60, p. 1466, 1995 DOI: 10.1021/jo00110a059

A methanolic solution of 0.5 M sodium methanolate (NaOMe/MeOH, 7.4 mL, 3.69 mmol) was slowly added dropwise to a solution of anhydrous tetrahydrofuran (12 mL) containing 3,6-dichloropyridazine (500 mg, 3.36 mmol), and the reaction mixture was stirred for 1 h at room temperature. Subsequently, the reaction was quenched by the addition of water. The reaction mixture was extracted with ethyl acetate and the organic phases were combined. The organic phase was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography to afford 6-methoxy-3-chloropyridazine (436 mg, 90% yield) as a white solid.1H NMR (400 MHz, CDCl3) δ 4.12 (s, 3H), 6.98 (d, J = 9.2 Hz, 1H), 7.38 (d, J = 9.2 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ 55.5 (d, J = 9.2 Hz, 1H). CDCl3) δ 55.2, 119.9, 130.6, 150.9, 164.2.

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