[H-].[H-].[H-].[H-].[Li+].[Al+3].[Al+3].[Cl-].[Cl-].[Cl-].[F:11][C:12]1[CH:27]=[CH:26][C:15]2[C:16](=O)[C:17]3[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=3[CH:19]=[CH:20][C:14]=2[CH:13]=1.O>O1CCCC1.C(Cl)Cl>[F:11][C:12]1[CH:27]=[CH:26][C:15]2[CH2:16][C:17]3[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=3[CH:19]=[CH:20][C:14]=2[CH:13]=1
LiAlH4 (0.0686 mol) was added dropwise to a suspension of AlCl3 (0.0718 mol) in tetrahydrofuran (75 ml), cooled on an ice-bath and under N2 atmosphere. The mixture was stirred for 10 minutes at 0° C. A solution of 2-fluoro-5H-dibenzo[a,d]cyclohepten-5-one (0.0653 mol and prepared as described in DE 3,644,462) in tetrahydrofuran (75 ml) was added dropwise and the resulting reaction mixture was allowed to warm to room temperature. Then, the reaction mixture was stirred and refluxed for 2 hours. The mixture was cooled on an ice-bath. Water and CH2Cl2 was added. The organic layer was washed with a saturated aqueous NaHCO3 solution, dried, filtered and the solvent was evaporated, yielding 13.16 g (96%) of 2-fluoro-5H-dibenzo[a,d]cycloheptene (intermediate 1)
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