[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-].[Br:11][C:12]1[CH:13]=[C:14]([CH:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)O)[CH:15]=[CH:16][CH:17]=1.Cl>CCOCC.COCCOC.CCO.CCOCC.CO>[CH2:18]([C:14]1[CH:15]=[CH:16][CH:17]=[C:12]([Br:11])[CH:13]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1
To a suspension of 422 mg (11.12 mmol, 1.31 eq.) lithium aluminum hydride in 30 ml dry ether a solution of 1.38 g (10.35 mmol, 1.22 eq.) aluminum chloride in 18 ml dry ether was added cautiously under stirring. After the complete addition the resulting mixture was stirred for 30 min at r.t. before a solution of 2.24 g (8.52 mmol) (3-Bromo-phenyl)-phenyl-methanol (prepared above) in 19 ml dry ether was added dropwise. Then the mixture was refluxed for 12 h and after that cooled to 0° C. in an ice-bath. After adding cautiously 10 ml of a mixture of ether/methanol (1:1) 28 ml 1 N HCl-solution was added and the mixture was extracted with ether. The comb. org. fractions were washed with brine, dried over Na2SO4 and evaporated. Column chromatography (PE/CH2Cl2 (9+1)) yielded 1.50 g (6.06 mmol, 71.17%) 1-Benzyl-3-bromo-benzene (87) as a colorless liquid.
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