[OH:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([C:11]([C:13]2[C:14]([C:19]([F:22])([F:21])[F:20])=[N:15][CH:16]=[CH:17][CH:18]=2)=[O:12])=[CH:4][C:3]=1[O:23]C.[Cl-].[Al+3].[Cl-].[Cl-].N1C=CC=CC=1.Cl>ClCCCl>[OH:23][C:3]1[CH:4]=[C:5]([C:11]([C:13]2[C:14]([C:19]([F:22])([F:20])[F:21])=[N:15][CH:16]=[CH:17][CH:18]=2)=[O:12])[CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=1[OH:1]To a stirred solution of (4-hydroxy-3-methoxy-5-nitrophenyl)(2-(trifluoromethyl)pyridin-3-yl)methanone (0.287 g, 0.84 mmol) in 1,2-dichloroethane (10 mL) cooled in an ice-water bath was added aluminium chloride (0.14 g, 1.05 mmol) in one portion followed by pyridine (0.26 g, 3.35 mmol) dropwise. The resulting red suspension was stirred at 80° C. for two hours, then cooled to room temperature and poured onto cold 2 N aqueous hydrochloric acid (100 mL). The precipitate was filtered off, washed with water and dried to give (3,4-dihydroxy-5-nitrophenyl)(2-(trifluoromethyl)pyridin-3-yl)methanone, 0.182 g, (66%).
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