反応 #928101

反応方程式

3,3,5-tribromooxindole

ammonium chloride

→

5-bromo-7-azaoxindole

溶媒

THF

反応条件

後処理

1. 1
   その他The flask is placed in a water bath
2. 2
   workup.ADDITIONis added
3. 3
   その他the zinc is removed by filtration through a pad of diatomaceous earth
4. 4
   その他The organic layer is separated
5. 5
   抽出the aqueous layer is extracted with THF (20 mL)
6. 6
   洗浄The combined organic layers were washed with saturated brine solution
7. 7
   乾燥dried over anhydrous magnesium sulfate
8. 8
   その他the solvent removed under reduced pressure
9. 9
   その他The brown residue is triturated with water (20 mL)
10. 10
    ろ過the tan solid is collected by filtration
11. 11
    その他dried under vacuum

実験手順

A solution of 3,3,5-tribromooxindole (5.0 g, 13.4 mmol) in fresh THF (100 mL) is stirred at room temperature and a saturated aqueous solution of ammonium chloride (100 mL) is added. The flask is placed in a water bath and activated zinc dust (15.0 g, 230 mmol) is added. The mixture is stirred for 20 min and the zinc is removed by filtration through a pad of diatomaceous earth. The organic layer is separated and the aqueous layer is extracted with THF (20 mL). The combined organic layers were washed with saturated brine solution, dried over anhydrous magnesium sulfate and the solvent removed under reduced pressure. The brown residue is triturated with water (20 mL) and the tan solid is collected by filtration and dried under vacuum to give 5-bromo-7-azaoxindole as a tan solid, 2.02 g (71%). 1H NMR (DMSO-d6) δ11.13 (s,1H), 8.15 (s,1H), 8.76 (s,1H), 3.57 (s, 2H). MS (AP−ve) 211 (100) (M−H).

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