4-Methoxyphenol → HCID 67386845, compound

Participants

Reaction Steps

To a solution of 1-(2-chloro-4-iodo-6-methylphenyl)ethanone (1.1 g, 3.7 mmol), K3PO4 (1.6 g, 7.4 mmol), and 4-methoxyphenol (0.55 g, 4.44 mmol) in DMF (55 mL) was added tetrabutylammomium bromide (0.12 g, 0.37 mmol) and copper(I) iodide (70 mg, 0.37 mmol). The reaction was heated at reflux for 22 h. The solution was extracted with EtOAc (10 mL), and the organic layer was separated, washed with H2O (11 mL), dried over MgSO4(s), and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel to give 1-[2-chloro-4-(4-methoxyphenoxy)-6-methylphenyl]ethanone as yellow oil in 19% yield: 1H NMR (500 MHz, CDCl3) δ 6.97 (m, 2H), 6.90 (m, 2H), 6.73 (d, J=2.19 Hz, 1H), 6.67 (d, J=1.99 Hz, 1H), 3.81 (s, 3H), 2.52 (s, 3H), 2.20 (s, 3H).

Provenance & Evidence