1-chloro-2-iodo-3-methylbenzene

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1-chloro-2-iodo-3-methylbenzene (7.5 g, 30 mmol) in 60 mL CCl4 stirred at 70° C. was treated with 1-bromopyrrolidine-2,5-dione (7.9 g, 45 mmol) and dibenzoyl peroxide (0.72 g, 3.0 mmol) slowly. The mixture was refluxed under a sunlight lamp for 15 hours. The mixture was cooled to room temperature, filtered through a plug of Celite, and rinsed with 10% EtOAc/hexane. The filtrate was concentrated and purified by column chromatography (0-10% EtOAc/hexane) to give 7.1 g pink oil. The mixture was refluxed under a sunlight lamp for 15 hours The mixture was cooled to room temperature filtered through a plug of Celite rinsed with 10% EtOAc/hexane The filtrate was concentrated purified by column chromatography (0-10% EtOAc/hexane)

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1-chloro-2-iodo-3-methylbenzene (7.5 g, 30 mmol) in 60 mL CCl4 stirred at 70° C. was treated with 1-bromopyrrolidine-2,5-dione (7.9 g, 45 mmol) and dibenzoyl peroxide (0.72 g, 3.0 mmol) slowly. The mixture was refluxed under a sunlight lamp for 15 hours. The mixture was cooled to room temperature, filtered through a plug of Celite, and rinsed with 10% EtOAc/hexane. The filtrate was concentrated and purified by column chromatography (0-10% EtOAc/hexane) to give 7.1 g pink oil. The mixture was refluxed under a sunlight lamp for 15 hours The mixture was cooled to room temperature filtered through a plug of Celite rinsed with 10% EtOAc/hexane The filtrate was concentrated purified by column chromatography (0-10% EtOAc/hexane)