Hydrogen Bromide → 1,2-Bis(4-nitrophenyl)ethane-1,2-dione

HRID 1267685Notes

Reaction equation

HRID 1267685 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

HCID 260Hydrogen BromideHCID 135241422-Benzoyloxy-1,2-bis(4-nitrophenyl)ethanone

Product 1

HCID 18120081,2-Bis(4-nitrophenyl)ethane-1,2-dioneYield 91%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

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.

Workup

  1. customInto a 500 mL three-necked, round-bottomed flask equipped with a magnetic stirrer
  2. stirringstirred at 60° C
  3. customDuring this process, light yellow crystals were separated from the reaction mixture
  4. temperatureto cool down on its own
  5. filtrationthe crystals were collected by suction filtration, 10.1 g (91% yield), mp 211-212° C

Sources & evidence

ORD record
ord-8b5f6150b8fc430e8d44588f0ca7e80d
Source dataset
uspto-grants-2003_04
Patent number
US06552195B1

Reaction notes

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