C([O:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)(=O)C=C.[Cl-].[Al+3].[Cl-].[Cl-].[Cl-].[Na+].Cl>>[F:12][C:9]1[CH:8]=[CH:7][C:6]([OH:5])=[C:11]2[C:10]=1[CH2:8][CH2:7][C:6]2=[O:5]4-Fluorophenyl acrylate (12.0 g) was added to a mixture of aluminum chloride (33.7 g) and sodium chloride (14.8 g), and the mixture was stirred at 80° C. for 2 hours and then at 160° C. for 1 hour. After completion of the reaction, ice-water and concentrated hydrochloric acid were added, and the reaction mixture was extracted with chloroform. The extract was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. The solvent was evaporated, and the resulting residue was purified by silica gel column chromatography. From the eluate of hexane-ethyl acetate (9:1), 4-fluoro-7-hydroxy-1-indanone (5.75 g) was obtained as a pale yellow powder.
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