Benzoyl Peroxide → 2-(Bromomethyl)-1-chloro-3-iodobenzene
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([I:8])[C:3]=1[CH3:9].[Br:10]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:10][CH2:9][C:3]1[C:4]([I:8])=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
A mixture of 1-chloro-3-iodo-2-methylbenzene (11 g, 44 mmol) in 60 mL CCl4 was stirred at 70° C. and treated with 1-bromopyrrolidine-2,5-dione (12 g, 65 mmol) and dibenzoyl peroxide (1.1 g, 4.4 mmol) slowly. The resulting mixture was refluxed for 15 hours. The mixture was cooled to room temperature, filtered through a plug of Celite, and washed with 10% EtOAc/hexane. The organic was concentrated and purified by column chromatography (0-10% EtOAc/hexane) to give 14 g pink solid.
Workup
- temperatureThe resulting mixture was refluxed for 15 hours
- temperatureThe mixture was cooled to room temperature
- filtrationfiltered through a plug of Celite
- washwashed with 10% EtOAc/hexane
- concentrationThe organic was concentrated
- custompurified by column chromatography (0-10% EtOAc/hexane)
Sources & evidence
- ORD record
- ord-49cdd5f5e99a4f42bae99b7545f8827f
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07635715B2
Reaction notes
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