Potassium Bromide → 8-bromo-5-cyclopropyl-2,3,5,6-tetrahydrobenzo[b][1,5]diazocin-4(1H)-one

Participants

Reaction Steps

Sodium perborate tetrahydrate (1.07 g, 6.94 mmol) was added in one portion to a suspension of KBr (0.770 g, 6.47 mmol), 5-cyclopropyl-2,3,5,6-tetrahydrobenzo[b][1,5]diazocin-4(1H)-one (1.00 g, 4.62 mmol) and ammonium molybdate tetrahydrate (0.114 mg, 0.092 mmol) in acetic acid (10 ml). The mixture was stirred at room temperature for 24 hours, then quenched with sodium carbonate (aqueous saturated) and a few drops of NaOH (10% aqueous). The mixture was extracted with ethyl acetate and the combined organic phases were washed with sodium carbonate, dried over sodium sulfate filtered and concentrated. Purification of the crude mixture by silica gel flash chromatography (0-20% methanol in ethyl acetate) gave the desired product as a brown solid (0.619 g, 45%).

Provenance & Evidence