[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:7])[CH3:6].[Cl:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[C:12]([Cl:18])[CH:11]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[C:12]([Cl:18])[C:11]=1[C:5](=[O:7])[CH3:6]A mixture of aluminum chloride (4.50 g, 33.9 mmol) and acetyl chloride (2.40 mL, 33.9 mmol) in CH2Cl2 (20.0 mL) was stirred at 0° C. for 30 min. The reaction mixture was slowly added with 1,3-dichloro-5-methoxybenzene (10-1, 2.00 g, 11.3 mmol) in CH2Cl2 (10.0 mL), and the resultant solution was stirred at room temperature for additional 2.0 h. The solution was basified with saturated aqueous NaHCO3. The organic layer was separated, dried over MgSO4(s), and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to give 1-(2,6-dichloro-4-methoxyphenyl)ethanone (10-2, 1.0 g, 4.6 mmol) as yellow oil in 40% yield: 1H NMR (CDCl3, 500 MHz) δ 7.01 (d, J=1.6 Hz, 2 H), 6.82 (d, J=1.6 Hz, 2 H), 3.83 (s, 3 H), 2.49 (s, 3 H).
Loading…
