N-bromobutanimide → HCID 13187506, compound
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:11]([O-:13])=[O:12])[CH:5]=[CH:6][C:7]=1[C:8](=[O:10])[CH3:9].C1C(=O)N([Br:21])C(=O)C1>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([N+:11]([O-:13])=[O:12])[CH:5]=[CH:6][C:7]=1[C:8](=[O:10])[CH2:9][Br:21]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
A stirring solution of 3-chloro-4-acetyl-nitrobenzene (1.685 g, 8.44 mmol) (prepared as described in J. Med. Chem. 2005, 48, 6066) and paratoluenesulfonic acid (2.41 g, 12.66 mmol) in acetonitrile (100 mL) was treated with NBS (1.503 g, 8.44 mmol) and heated to 80° C. for 23 h. Another gram of NBS was added after 21 h. The reaction was cooled to room temperature and concentrated in vacuo. The residue was taken up in EtOAc and the organic layer was washed with water (2×), brine, and dried over MgSO4, filtered, and adsorbed on silica. Purification on silica by flash chromatography using a gradient of 0-40% EtOAc/hexane yielded 554 mg of the titled compound as a waxy solid (23% yield): 1H NMR (400 MHz, DMSO-d6) δ 4.95 (s, 2H), 8.09 (d, 1H), 8.35 (dd, 1H), 8.44 (d, 1H).