[Cl:1][C:2]1[C:3]([CH3:15])=[C:4]([CH:13]=[CH2:14])[C:5]([O:11][CH3:12])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.Cl[C:17](Cl)(Cl)[C:18](Cl)=[O:19].P(Cl)(Cl)(Cl)=O>CCOCC.COCCOC.C(O)(=O)C.O.[Cu].[Zn].[Zn]>[C:8]([C:6]1[C:5]([O:11][CH3:12])=[C:4]([CH:13]2[CH2:17][C:18](=[O:19])[CH2:14]2)[C:3]([CH3:15])=[C:2]([Cl:1])[CH:7]=1)(=[O:10])[CH3:9]To a solution of 1-(5-chloro-2-methoxy-4-methyl-3-vinylphenyl)ethanone (530 mg, 2.4 mmol) in ether (10 mL) was added zinc-copper couple (1.8 g, 14 mmol). The reaction mixture was heated at 40° C. and a solution of trichloroacetyl chloride (1.4 mL, 13 mmol) and phosphoryl chloride (1.2 mL, 13 mmol) in 1,2-dimethoxyethane (3 mL) was added slowly over 2 h. After addition, the reaction mixture was stirred under reflux overnight. The reaction was quenched with saturated NaHCO3 solution and diluted with ether. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated. The residue and zinc (0.31 g, 4.7 mmol) in acetic acid (10 mL) was stirred at room temperature for 2 h and then reflux overnight. Another portion of zinc was added and reflux for another 4 h. The mixture was diluted with water and extracted with ether. The organic phase was washed successively with a saturated NaHCO3 solution, water and brine, then dried over MgSO4 and concentrated. The crude material was purified with flash chromatography (eluting with 0 to 30% ethyl acetate in hexanes) to give the desired product (0.17 g, 27%). LCMS calculated for C14H16ClO3 (M+H)+: m/z=267.1; Found:267.0
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