Réaction #9415

Équation de réaction

sodium hydrogen carbonate

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

sodium acetate

bromine

→

subtitled compound

Rendement 105.0%

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

Rendement 105.0%

Solvants

acetic acid

acetic acid

Conditions de réaction

Traitement

1. 1
   Extractionextracted with EtOAc (×2)
2. 2
   Lavagethe combined organic layers were washed with water, sat. sodium hydrogen carbonate solution, water
3. 3
   Séchagedried (MgSO4)
4. 4
   Autreevaporated

Mode opératoire

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).

Source