Br[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10](=[O:19])/[CH:11]=[CH:12]/[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O.Cl[Pd]Cl>[CH3:9][O:8][C:6]1[CH:7]=[C:2]2[C:3](=[CH:4][CH:5]=1)[C:10](=[O:19])[CH:11]=[C:12]2[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1To a solution of (E)-1-(2-bromo-4-methoxyphenyl)-3-phenyl-2-propen-1-one (6.0 g, 18.91 mmol) obtained in Step 2 in DMF (15 mL) was added PPh3 (1.46 g, 5.68 mmol, 0.3 eq), K2CO3 (5.23 g, 37.83 mmol, 2 eq), and PdCl2 (335 mg, 1.89 mmol, 0.1 eq). The reaction vial was heated to 110° C. for 3 h. After cooling to room temperature, the reaction mixture was diluted with EtOAc and filtered through a Celite pad. The solution was washed with H2O and brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexanes=1:5) to afford the desired product (2.8 g, 63%).
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