[Cl-].[Al+3].[Cl-].[Cl-].[CH2:5]([OH:7])[CH3:6].C(Cl)(=O)C.[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][CH3:20]>C(Cl)(Cl)Cl.O>[CH3:6][C:5]([C:17]1[CH:16]=[CH:15][C:14]([O:19][CH3:20])=[C:13]([Cl:12])[CH:18]=1)=[O:7]Anhydrous aluminum chloride (281 g, 2.104 mol) and 1 L of ethanol-free chloroform were maintained at 0° C. with an ice bath while a solution of acetyl chloride (162 g, 2.28 mol) in 300 mL of chloroform was added over 25 minutes. To this solution was added 2-chloroanisole (250 g, 1.75 mol) in 250 mL of chloroform over 1 hour. The solution was stirred at room temperature for 16 hours and was poured into a mixture of ice and water. The phases were separated and the aqueous phase was extracted with dichloromethane and combined with the original organic phase. The combined organics were dried over anhydrous MgSO4, filtered and concentrated in vacuo to afford a solid which was crystallized from dichloromethane/hexane to give 3-chloro-4-methoxyacetophenone (246 g, 76%) which was used directly in the next step without further purification.
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