反応 #9415

反応方程式

sodium hydrogen carbonate

spiro[cyclopentane-1,3′-[3H]indol]-2′(1′H)-one

sodium acetate

bromine

→

subtitled compound

収率 105.0%

5-Bromo-spiro[cyclopentane-1,3′-[3H]indol]-2′(1′H)-one

収率 105.0%

溶媒

acetic acid

acetic acid

反応条件

後処理

1. 1
   抽出extracted with EtOAc (×2)
2. 2
   洗浄the combined organic layers were washed with water, sat. sodium hydrogen carbonate solution, water
3. 3
   乾燥dried (MgSO4)
4. 4
   その他evaporated

実験手順

A solution of spiro[cyclopentane-1,3′-[3H]indol]-2′(1′H)-one (0.27 g, 1.4 mmol) and sodium acetate (0.12 g, 1.46 mmol) in acetic acid (10 cm3) was treated with bromine (0.24 g, 1.51 mmol) in acetic acid (2 cm3). After 30 min. the mixture was poured into sat. sodium hydrogen carbonate solution and extracted with EtOAc (×2), the combined organic layers were washed with water, sat. sodium hydrogen carbonate solution, water, dried (MgSO4), and evaporated to give the subtitled compound (0.37 g, 1.47 mmol, 96%) as an off-white solid which was used without further purification: 1H NMR (CDCl3) δ 1.8–2.27 (m, 8H), 6.79 (d, J=8 Hz, 1H), 7.30–7.39 (m, 2H), 8.63 (br s, 1H).

出典