[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH3:12])[C:10]#[N:11])[CH:5]=[CH:6][C:7]=1[Cl:8].B.C1COCC1.CCO.Cl>C1COCC1.CCOCC.O>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH3:12])[CH2:10][NH2:11])[CH:5]=[CH:6][C:7]=1[Cl:8]
2-(3,4-Dichloro-phenyl)-propionitrile (5.0 g, 25.0 mmol) was dissolved in THF (80 mL). BH3.THF (1 M in THF, 27.5 mL, 27.5 mmol) was added and the mixture was stirred overnight at rt. EtOH (10 mL) was added, the mixture was stirred for 20 min, and HCl in Et2O (2 M, 12.5 mL) was added. After stirring for 1 h, water was added, causing precipitation of the product. The product was collected by suction filtration and dried (4.2 g, 70%). MS (ESI+): mass calcd. for C9H11Cl2N, 204.1; m/z found, 205 [M+H]+. 1H NMR (400 MHz, CD3OD): 7.45-7.42 (m, 2H), 7.17-7.15 (m, 1H), 3.05-3.02 (m, 2H), 2.98-2.96 (m, 1H), 1.24 (d, J=6.5, 3H).
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