Phenol → 3-Chloro-6-phenoxypyridazine

Participants

Reaction Steps

3,6-Dichloropyridazine (Aldrich, 4.47 g, 30 mmol) in NaOH (10%, 20 mL) was treated with phenol (Aldrich, 1.88 g, 20 mmol) at 100° C. for 15 hours. After cooling to room temperature, the mixture was extracted with ethyl acetate (2×50 mL). The extracts were combined and concentrated under reduced pressure. The title compound was purified by chromatography (SiO2, Hexanes: ethyl acetate=80: 20, Rf. 0.5) as a solid (3.8 g, yield, 92%). 1H NMR (CDCl3, 300 MHz) δ 7.11–7.29 (m, 3H), 7.38–7.55 (m, 4H) ppm. MS (DCl/NH3) m/z 207 (M+H)+, 209 (M+H)+.

Provenance & Evidence