Hydrogen Bromide → 1,2-Bis(4-nitrophenyl)ethane-1,2-dione
Reaction equation
C([O:9][CH:10]([C:22]1[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=1)[C:11]([C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1)=[O:12])(=O)C1C=CC=CC=1.Br>CS(C)=O>[N+:19]([C:16]1[CH:17]=[CH:18][C:13]([C:11]([C:10]([C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=2)=[O:9])=[O:12])=[CH:14][CH:15]=1)([O-:21])=[O:20]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Into a 500 mL three-necked, round-bottomed flask equipped with a magnetic stirrer, dropping funnel and nitrogen inlet, 2-benzoyloxy-1,2-bis(4-nitrophenyl)ethanone (15.0 g, 36.9 mmol) was dissolved in DMSO (dimethyl sulfoxide) (150 mL) and stirred until the solution become homogeneous. Then, hydrobromic acid (48%, 50 mL) was added through dropping funnel and stirred at 60° C. During this process, light yellow crystals were separated from the reaction mixture. After the reaction mixture had been allowed to cool down on its own, the crystals were collected by suction filtration, 10.1 g (91% yield), mp 211-212° C. Anal. Calcd. for C21H12N4O6: C, 56.01%; H, 2.69%; N, 9.33%; O, 31.97%. Found: C, 55.75%; H, 2.50%; N, 9.30%; O, 33.98%: FT-IR (KBr, cm−1): 1347, 1527, 1682. Mass spectrum (m/e): 282 (M+, 100% relative abundance). 1H-NMR (DMSO-d6, δ in ppm): 8.27-8.30 (dd, 4H, Ar), 8.41-8.44 (dd, 4H, Ar). 13C-NMR (DMSO-d6, δ in ppm) 123.94, 131.66, 136.81, 150.75, 190.06.