Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]#[N:10].[C:11]([C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1)([OH:13])=[O:12].C(=O)([O-])[O-].[K+].[K+]>O.O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:9]([CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:17]1[CH:18]=[CH:19][C:14]([C:11]([OH:13])=[O:12])=[CH:15][CH:16]=1)#[N:10]A stirred mixture containing 5.88 g (0.03 mol) of (2-bromo-phenyl)-acetonitrile, 4.978 g. (0.03 mol) of 4-carboxyphenylboronic acid, 8.29 g (0.06 mol) of potassium carbonate and 0.52 g of dichlorobis(triphenylphosphine)palladium(II) in 46 mL of water and 25 mL of 1,4-dioxane was heated under reflux for two hours in an atmosphere of nitrogen. The reaction mixture was allowed to cool to room temperature and filtered. The dioxane was removed in vacuo and the residue diluted with 100 mL of water and then acidified with 20% hydrochloric acid. The crude product (1.2g) was recrystallized from ethanol to give a solid, m.p. 218-220° C.
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