[CH3:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:12])[CH3:11])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[Cl:13][CH2:14][C:15](Cl)=[O:16].[Al+3].[Cl-].[Cl-].[Cl-]>C(=S)=S>[Cl:13][CH2:14][C:15]([C:7]1[C:6]([CH3:8])=[CH:5][C:4]([NH:9][C:10](=[O:12])[CH3:11])=[CH:3][C:2]=1[CH3:1])=[O:16]To a solution of N-(3,5-dimethylphenyl)acetamide (4.0 g, 24.5 mmol) and ClCH2COCl (4.2 g, 37 mmol) in CS2 (30 mL), AlCl3 (10.0 g, 74.9 mmol) was added in portions. The resulting mixture was refluxed overnight. The reaction mixture was then cooled down to room temperature before the CS2 layer was decanted. The resulting complex was decomposed by pouring onto a mixture of ice (500 g) and concentrated HCl (30 mL). The solid was collected by suction, washed with 1N HCl and water, and recrystallized in EtOH to afford N-(4-(2-chloroacetyl)-3,5-dimethylphenyl)acetamide as a brown powder (3.4 g, 57.9%), which was used without further purification.
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