反応 #1702081

反応方程式

Sodium perborate tetrahydrate

KBr

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

→

desired product

収率 45.4%

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

収率 45.4%

溶媒

acetic acid

反応条件

後処理

1. 1
   その他quenched with sodium carbonate (aqueous saturated) and a few drops of NaOH (10% aqueous)
2. 2
   抽出The mixture was extracted with ethyl acetate
3. 3
   洗浄the combined organic phases were washed with sodium carbonate
4. 4
   乾燥dried over sodium sulfate
5. 5
   ろ過filtered
6. 6
   濃縮concentrated
7. 7
   その他Purification of the crude mixture by silica gel flash chromatography (0-20% methanol in ethyl acetate)

実験手順

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%).

出典