反応 #611138

反応方程式

4-amino-2,2-diflouro-1,3-benzodioxole

N-bromosuccinimide

→

5-bromo-4-amino-2,2-diflouro-1,3-benzodioxole

収率 64.2%

溶媒

dichloromethane

反応条件

後処理

1. 1
   workup.WAITat room temperature for 1 h
2. 2
   その他The reaction mixture was quenched with 1M sodium thiosulfate solution
3. 3
   workup.ADDITIONdiluted with deionized water
4. 4
   抽出extracted with dichloromethane (2×50 mL)
5. 5
   乾燥The combined organic layers were dried (Na2SO4)
6. 6
   ろ過filtered
7. 7
   濃縮concentrated in vacuo
8. 8
   その他The crude product was purified by flash chromatography (SiO2, 0-20% ethyl acetate in hexanes)
9. 9
   その他to recover

実験手順

To a stirred solution of 4-amino-2,2-diflouro-1,3-benzodioxole (2.5 g, 14.4 mmol) in dichloromethane at 0° C. was added N-bromosuccinimide (2.7 g, 15.2 mmol) portion wise. The solution was stirred at 0° C. for 30 min, then at room temperature for 1 h. The reaction mixture was quenched with 1M sodium thiosulfate solution and diluted with deionized water, extracted with dichloromethane (2×50 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was purified by flash chromatography (SiO2, 0-20% ethyl acetate in hexanes) to recover starting material 1 g and afford 5-bromo-4-amino-2,2-diflouro-1,3-benzodioxole as colorless oil (2.33 g, 9.25 mmol, 64%). MS: (ES) m/z calculated for C7H4BrF2NO [M+H]+252.0. found 252.

出典