N-bromobutanimide → HCID 10709162, compound
Reaction equation
[Br:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[CH:11]=[C:12]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH:13]=[CH:14][C:15]=1[Cl:16]>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.ClCCCl>[Cl:9][C:10]1[CH:11]=[C:12]([CH:17]([Br:1])[C:18]([O:20][CH3:21])=[O:19])[CH:13]=[CH:14][C:15]=1[Cl:16]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 85 °C
Procedure
N-bromosuccinimide (116 g, 1.4 equivalent amounts) was added to a 1,2-dichloroethane (320 mL) solution of methyl 2-(3,4-dichlorophenyl)acetate (106.8 g, 0.446 mol) at room temperature, followed by heating to 85° C. To this solution, a 1,2-dichloroethane (22.6 mL) solution of benzoyl peroxide (2.26 g, 2.0 mol %) was dropwise added dividedly 10 times every 10 minutes, followed by stirring at 85° C. for 3 hours. The reaction solution was cooled to room temperature, sequentially washed with a 2M sodium hydroxide aqueous solution, a mixed liquid of water-sodium thiosulfate aqueous solution (2:1, (v/v)), a saturated ammonium chloride aqueous solution and a saturated salt solution, and dried over anhydrous magnesium sulfate. The drying agent was removed by filtration, and the solvent was distilled off to give the desired product as a brown oil (142 g, yield: 103%).
Workup
- temperatureThe reaction solution was cooled to room temperature
- washsequentially washed with a 2M sodium hydroxide aqueous solution
- dry with materiala mixed liquid of water-sodium thiosulfate aqueous solution (2:1, (v/v)), a saturated ammonium chloride aqueous solution and a saturated salt solution, and dried over anhydrous magnesium sulfate
- customThe drying agent was removed by filtration
- distillationthe solvent was distilled off
Sources & evidence
- ORD record
- ord-ec0defa794d449d28b4b534735ef73a4
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08642786B2
Reaction notes
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