[OH-].[Na+].[CH3:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][CH:7]=1)=O.[CH:13](=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(C1C=CC=CC=1)(=O)C>O.C(O)C>[Br:12][C:9]1[CH:10]=[CH:11][C:6]([CH:4]=[CH:3][C:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:20])=[CH:7][CH:8]=1Sodium hydroxide (1.88 g, 47 mmol) and 4-bromoacetophenone (7.47 g, 37.5 mmol) were dissolved in water (15 mL) and ethanol (50 mL). Benzaldehyde (4.00 g, 37.5 mmol) dissolved in ethanol (20 mL) was added dropwise to the acetophenone solution. A slurry quickly formed, which was allowed to stir overnight. The slurry was filtered, was with water until the filtrate was neutral to pH paper, and dried at 100° C. for 12 hours. A light tan solid was obtained (10.0 g, 93% yield).
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