4-Methoxybenzenethiol → HCID 86690818, compound

Participants

Reaction Steps

A mixture of 1-(2-chloro-4-iodo-6-methylphenyl)ethanone (3-1, 0.720 g, 2.44 mmol), 4-methoxybenzenethiol (0.45 mL, 3.7 mmol), copper(I) oxide (17.0 mg, 0.12 mmol), and potassium hydroxide (0.34 g, 6.1 mmol) in DMF (2.2 mL) and H2O (0.5 mL) was heated at reflux for 20 h. The mixture was quenched with H2O and extracted with ethyl acetate. The organic layer was collected, dried over MgSO4(s), and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to provide 1-(2-chloro-4-(4-methoxyphenylsulfanyl)-6-methylphenyl)ethanone (3-2, 0.10 g, 0.33 mmol) as yellow oil in 13% yield: 1H NMR (500 MHz, CDCl3) δ 7.44 (d, J=8.7 Hz, 2 H), 6.94 (d, J=8.7 Hz, 2 H), 6.86 (d, J=8.2 Hz, 2 H), 3.85 (s, 3 H), 2.50 (s, 3 H), 2.17 (s, 3 H).

Provenance & Evidence