Azobisisobutyronitrile → 3-Bromo-6-chloro-inden-1-one

Participants

Reaction Steps

To a solution of 6-chloro-1-indanone (II) (100.0 g, 600.2 mmol) in 1,2-dichloroethane (1.00 L) was added 2,2′-azo-bis-isobutyronitrile (9.86 g, 60.0 mmol) followed by N-bromosuccinimide (224.3 g, 1.26 mol). The reaction mixture was quickly heated to reflux. After 30 min at reflux, more 2,2′-azo-bis-isobutyronitrile (9.86 g, 60.0 mmol) was added. The reaction mixture was kept for 4.5 h at reflux. Afterwards the mixture was stirred at room temperature overnight. The mixture was cooled to 0° C., and triethylamine (126 mL, 904 mmol) was added dropwise. The mixture was stirred for 1 h at 0° C., and then allowed to heat to room temperature. Water (1.0 L) was added. The mixture was vigorously stirred for 15 min. The stirring was stopped, and the aqueous layer was removed by suction. Fresh water (1.0 L) was added, and the mixture was stirred for 15 min. The aqueous layer was then separated by suction. The organic phase was further shaken with brine (500 mL) in a separating funnel.

Provenance & Evidence