[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][CH:3]=1.[CH:9]([Mg]Cl)([CH3:11])[CH3:10].[CH3:14][N:15]([CH3:28])[C:16]1(C#N)[CH2:25][CH2:24][C:19]2([O:23]CCO2)[CH2:18][CH2:17]1.[Cl-].[NH4+]>C(OCC)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:16]2([N:15]([CH3:14])[CH3:28])[CH2:17][CH2:18][C:19]([CH2:10][CH2:9][C:11]3[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=3)([OH:23])[CH2:24][CH2:25]2)=[CH:4][CH:3]=126.6 g 4-bromoiodobenzene were placed in 150 ml diethylether and 47 ml 2.0 molar isopropyl magnesium chloride solution were added dropwise at ambient temperature. After one further hour, 18 g 8-dimethylamino-1,4-dioxaspiro[4.5]decane-8-carbonitrile, dissolved in 250 ml diethylether, were added dropwise and stirred overnight. To work up the mixture with ice cooling, 20 ml ammonium chloride solution (20% by weight) were added, extracted three times with 100 ml diethylether in each case, the combined organic phases were dried over sodium sulfate, filtered, concentrated and substantially freed of solvent residues under vacuum. The crude product (21.8 g) obtained was chromatographed with diethylether over silica gel. 7.49 g 4-(4-bromophenyl)-4-dimethylamino-1-phenethylcyclohexanol were obtained as a colorless liquid.
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