Azobisisobutyronitrile → HCID 22258788, compound
Reaction equation
[N+:1]([C:4]1[C:13]2[CH2:12][O:11][CH2:10][O:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-:3])=[O:2].BrN1[C:19](=[O:20])[CH2:18]CC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N.[O-]CC.[Na+]>C(Cl)(Cl)(Cl)Cl.C(O)C>[CH2:19]([O:20][CH:12]1[C:13]2[C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=[CH:7][C:8]=2[O:9][CH2:10][O:11]1)[CH3:18]Participants
Conditions
- Temperature
- 100 °C
Procedure
To a stirred solution of 5-nitro-4H-1,3-benzodioxine (10.0 g, 55.203 mmol) in carbon tetrachloride (70 mL) were added N-bromosuccinimide (10.808 g, 60.723 mmol) and 2,2′-azobisisobutyronitrile (0.906 g, 5.520 mmol). The mixture was stirred at 100° C. for 2 hrs. After cooled to room temperature, a solution of sodium ethoxide (4.884 g, 71.764 mmol) in ethanol (70 mL) was added to the mixture, and the stirring was continued at room temperature for 3 hrs. The reaction was quenched with water and extracted with ethyl acetate. The organic phase was washed with brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=9/1) to give 4-ethoxy-5-nitro-4H-1,3-benzodioxine as a pale yellow oil (10.8 g, yield; 87%).
Workup
- temperatureAfter cooled to room temperature
- waitthe stirring was continued at room temperature for 3 hrs
- customThe reaction was quenched with water
- extractionextracted with ethyl acetate
- washThe organic phase was washed with brine
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe residue was purified by column chromatography on silica gel (hexane/ethyl acetate=9/1)
Sources & evidence
- ORD record
- ord-a86d060e81ba484aa5b4c227204081de
- Source dataset
- uspto-grants-2006_01
- Patent number
- US06984649B1
Reaction notes
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