Br[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH3:9].[C:10](=[O:13])([O-])[O-].[Cs+].[Cs+].CN([CH:19]=[O:20])C>O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:10][O:13][C:19]([C:2]1[CH:7]=[CH:6][C:5]([C:2]2[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=2[CH3:9])=[CH:4][CH:3]=1)=[O:20]To a solution of 4-bromo-3-methyl phenol (0.300 g, 1 equiv) in DMF (5 mL) are added 4-methylester phenyl boronic acid (0.58 g, 2 equiv), dppf (0.27 g, 0.3 equiv), palladium acetate (0.036 g, 0.1 equiv), and cesium carbonate (1.04 g, 2 equiv). The reaction mixture is heated to 75° C. for 1 h. The reaction is cooled to room temperature and is diluted with water. The resulting solution is extracted with ethyl acetate. The combined organic layers are combined and washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue is purified via flash chromatography eluting with 3% ethyl acetate in toluene to give the desired product (0.224 g, 58%). ES/MS m/e 241.3 (M−1).
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