1-Bromo-3-chloropropane → HCID 18782780, compound

Reaction equation

[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[NH:8][C:9]3[C:14]([C:15]=2[CH:16]=1)=[CH:13][CH:12]=[CH:11][CH:10]=3)(=[O:3])[CH3:2].[H-].[Na+].Br[CH2:20][CH2:21][CH2:22][Cl:23]>CN(C=O)C>[Cl:23][CH2:22][CH2:21][CH2:20][N:8]1[C:7]2[CH:6]=[CH:5][C:4]([C:1](=[O:3])[CH3:2])=[CH:16][C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2

Participants

Procedure

3-Acetylcarbazole (1.0 g, 0.0048 mol) was dissolved in dry DMF (20 mL) and NaH (50% in oil) (0.13 g, 0.0053 mol) was added. The resulting mixture was stirred at room temperature for 1 h. The reaction mixture was added dropwise to a solution of 1-bromo-3-chloropropane (0.83 g, 0.0053 mol) in DMF (20 mL). The resulting mixture was stirred under a N2 atmosphere for 60 h. The solvent was removed in vacuo, and the residue was purified on a silica gel column (Eluent: CH2Cl2). This afforded the title comoound 0.70 g (51%) as a solid. M.p. 109-111° C.