Reacción #1702081

Ecuación de reacción

Sodium perborate tetrahydrate

KBr

5-cyclopropyl-2,3,5,6-tetrahydrobenzo[b][1,5]diazocin-4(1H)-one

→

desired product

Rendimiento 45.4%

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

Rendimiento 45.4%

Disolventes

acetic acid

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroquenched with sodium carbonate (aqueous saturated) and a few drops of NaOH (10% aqueous)
2. 2
   ExtracciónThe mixture was extracted with ethyl acetate
3. 3
   Lavadothe combined organic phases were washed with sodium carbonate
4. 4
   Secadodried over sodium sulfate
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated
7. 7
   OtroPurification of the crude mixture by silica gel flash chromatography (0-20% methanol in ethyl acetate)

Procedimiento

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%).

Fuente