Br[C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[C:5]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)=[O:6].[C:18]([O:22][CH2:23][CH3:24])(=[O:21])[CH:19]=[CH2:20].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:14][O:13][C:10]1[CH:11]=[CH:12][C:7]([C:5]([C:4]2[CH:3]=[C:2]([CH:17]=[CH:16][CH:15]=2)[CH:20]=[CH:19][C:18]([O:22][CH2:23][CH3:24])=[O:21])=[O:6])=[CH:8][CH:9]=1A mixture of 3-bromo-4'-methoxybenzophenone (Allen, Schumann, Day and Van Campen, J. Amer. Chem. Soc., 1958, 80, 591) (14.6 g), ethyl acrylate (25.3 g), palladium (II) acetate (100 mg), triphenylphosphine (225 mg) and triethylamine (2.65 g) in acetonitrile (20 mL) was heated in a stainless steel autoclave under a nitrogen atmosphere at 155° for 5 hours. After cooling, water was added and the precipitated solid was recrystallized from methanol to yielded ethyl 3-(4-methoxy benzoyl)cinnamate, m.p. 71°-71.5° (5.6 g).
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