Reacción #9415

Ecuación de reacción

sodium hydrogen carbonate

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

sodium acetate

bromine

→

subtitled compound

Rendimiento 105.0%

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

Rendimiento 105.0%

Disolventes

acetic acid

acetic acid

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted with EtOAc (×2)
2. 2
   Lavadothe combined organic layers were washed with water, sat. sodium hydrogen carbonate solution, water
3. 3
   Secadodried (MgSO4)
4. 4
   Otroevaporated

Procedimiento

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).

Fuente