[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][C:3]=1[O:11][CH3:12].B.Cl>O1CCCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH2:10])=[CH:4][C:3]=1[O:11][CH3:12]4-Bromo-3-methoxyphenylacetonitrile (22.6 g, 0.1 m) dissolved in tetrahydrofuran (100 ml) is added to 1M borane in tetrahydrofuran (300 ml) stirred at 25°. The mixture is refluxed, cooled to 0° and treated cautiously with 2N hydrochloric acid to give 4-bromo-3-methoxyphenethylamine.
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