4-Fluorophenol → 6-(4-Fluorophenoxy)phthalazin-1-ol

Participants

Reaction Conditions

Reaction Steps

A 100-mL round-bottom flask under argon was charged with 6-bromophthalazin-1-ol (0.5 g, 2 mmol), 4-fluorophenol (0.4 mL, 4 mmol), 2,2,6,6-tetramethyl-3,5-heptanedione (0.04 mL, 0.2 mmol), cesium carbonate (1 g, 4 mmol), and 1-methyl-2-pyrrolidinone (4 mL), followed by copper (I) chloride (0.1 g, 1 mmol). The reaction mixture was heated at 120° C. for 20 h. The reaction mixture was cooled, diluted with dichloromethane, and washed with water. The pH of the aqueous layer was adjusted to ˜7 with saturated aqueous NaHCO3 and extracted with DCM (2×). The combined organic extracts were dried (MgSO4), filtered, and concentrated in vacuo. Flash chromatography eluting with 1%, 2%, 3%, and 5% MeOH/CHCl3 gave the title compound. MS (ES+): 257.1 (M+H)+.

Provenance & Evidence