Acetonitrile → 4-bromo-5-(4-chlorophenyl)-1-methyl-1H-imidazole
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH3:13])[CH:10]=CN=2)=[CH:4][CH:3]=1.C1C(=O)N([Br:21])C(=O)C1.[C:22](#[N:24])C>>[Br:21][C:22]1[N:24]=[CH:10][N:9]([CH3:13])[C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1Participants
4
Conditions
- Temperature
- 0 °C
Procedure
(4-Chlorophenyl)-1-methyl-1H-imidazole (3 g, 15.5 mmol) was dissolved in ACN (150 mL) and cooled to 0° C. NBS (2.76 g, 15.5 mmol) was added in 3 portions over 5 min. The reaction was stirred at 0° C. for 20 min then let warm to ambient temperature. Solvents were removed in vacuo and the residue partitioned between EtOAc and 20% aqueous KH2PO4. The organics were separated, washed with saturated aqueous NaHCO3, and dried with saturated aqueous NaCl. Solvents were removed in vacuo and the residue purified by column chromatography on silica to provide the desired product. MS (m/z) 273.1 [M+H]+.