[Cl:1][CH2:2][C:3](=[O:13])[CH2:4][C:5]1[CH:10]=[CH:9][C:8](Cl)=[C:7](Cl)[CH:6]=1.[Cl:14]C1C=CC=CC=1CCl.II.ClCC(Cl)=O>[Zn].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][CH2:2][C:3](=[O:13])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[Cl:14]
The procedure described above for the synthesis of 1-chloro-3-(3,4-dichlorophenyl)propan-2-one was followed, reacting 2-chlorobenzyl chloride (1.6 mL, 2.0 g, 12 mmol) with zinc dust (1.22 g, 18.6 mmol) in the presence of iodine (0.157 g, 0.620 mmol), then with chloroacetyl chloride (1.5 mL, 2.1 g, 19 mmol) in the presence of Pd(PPh3)4 (0.287 g, 0.248 mmol). Flash chromatography over silica gel (10% ethyl acetate in hexanes) gave product of sufficient purity to be used in the next step (0.556 g, 22% yield): 1H NMR (400 MHz, CDCl3) δ 4.03 (s, 2H) 4.19 (s, 2H) 7.19-7.29 (m, 3H) 7.38-7.42 (m, 1H).
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