Iodine → 6-Fluoro-3-iodo-4,5-dihydro-1H-benzo[b]azepin-2(3H)-one

Participants

Reaction Conditions

Reaction Steps

6-Fluoro-1,3,4,5-tetrahydro-1-benzazepin-2-one (25 g, 140 mmol) was charged to a 100-mL three neck flask with a dropping funnel and an overhead stirrer. DCM (250 ml) is added and the reaction is cooled to 0° C. TMEDA (29.5 ml, 195 mmol) is added, followed by drop wise addition of iodotrimethylsilane (26.6 ml, 195 mmol). The mixture was stirred for 45 minutes. Iodine (49.6 g, 195 mmol) is added in 5 portions and the mixture is stirred for another 1.5 h. The reaction was quenched with 250 mL Na2SO3 (aqueous solution). The solids were dissolved in dichloromethane and the layers separated. The organic layer is washed with water, dried over Na2SO4, and concentrated to give 6-fluoro-3-iodo-1,3,4,5-tetrahydro-1-benzazepin-2-one (42.5 g) as a brown solid.

Provenance & Evidence