Реакция #1702081

Уравнение реакции

Sodium perborate tetrahydrate

KBr

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

→

desired product

Выход 45.4%

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

Выход 45.4%

Растворители

acetic acid

Условия реакции

Обработка

1. 1
   Другоеquenched with sodium carbonate (aqueous saturated) and a few drops of NaOH (10% aqueous)
2. 2
   ЭкстракцияThe mixture was extracted with ethyl acetate
3. 3
   Промывкаthe combined organic phases were washed with sodium carbonate
4. 4
   Сушкаdried over sodium sulfate
5. 5
   Фильтрацияfiltered
6. 6
   Концентрированиеconcentrated
7. 7
   ДругоеPurification of the crude mixture by silica gel flash chromatography (0-20% methanol in ethyl acetate)

Методика

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%).

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