[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[Na].[Br:17][CH2:18][CH2:19][CH2:20][Cl:21]>CN(C=O)C>[Cl:21][CH2:20][CH2:19][CH2:18][N:12]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[C:13]1=[CH:1][CH:2]=[CH:3][CH:4]=2.[Br:17][CH2:18][CH2:19][CH2:20][N:12]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[C:13]1=[CH:1][CH:2]=[CH:3][CH:4]=2Carbazole (50.0 g, 0.3 mol) was dissolved in dry DMF (1.5 L). NaH (60% in oil, 18.8 g, 0.45 mol) was added under a nitrogen atmosphere. The reaction mixture was stirred at ambient temperature for 3 h. To the resulting sodium salt was carefully added under vigorous stirring a solution of 1-bromo-3-chloropropane in dry DMF (0.5 L). The mixture was stirred at room temperature for 10 h. The solvent was removed in vacuo. The residual oil was dissolved in CH2Cl2 (350 mL), washed with water (3×100 ml), dried (MgSO4), filtered and the solvent removed in vacuo to give a yellow oil. The oil was triturated with cold n-heptane (3×50 mL), and the precipitate collected. This afforded the title compound (48.3 g, 66%) as a yellow solid. M.p. 39-40° C. 1H-NMR (δ CDCl3): 2.3-2.5 (m, 2H); 3.4 (t, 1H); 3.55 (t, 1H); 4.55 (d, t, 2H); 7.35 (m, 2H); 7.5 (d, 2H); 8.1 (d, 2H). The product was isolated as an 1:1 mixture of the 3-bromo- and 3-chloro-derivatives.
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