CCOCC.[Br:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]([N:16]([CH3:18])[CH3:17])=O)=[CH:9][CH:8]=1.CCOCC.C1COCC1.[OH-].[Na+]>O>[Br:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:13][CH2:14][N:16]([CH3:17])[CH3:18])=[CH:11][CH:12]=1To a suspension of LiAlH4in ether (5 mL) was added a solution of 2-(4-bromophenyl)-N,N-dimethylacetamide (1.1 g, 4.5 mmol) in 5:1 ether/THF (12 mL), giving a small exotherm. The mixture was stirred at room temperature for 3 h, refluxed overnight then cooled to 0° C. Water (0.5 mL) was added dropwise and the mixture stirred vigourously for 3 h, then poured into 1 M NaOH and extracted with ether. The organic phase was washed with brine and dried over MgSO4. Purification by flash chromatography (4% to 8% MeOH/dichloromethane+0.5% ammonium hydroxide) provided 132 mg of 2-(4-bromophenyl)-N,N-dimethylethanamine.
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