Reaktion #9415

Reaktionsgleichung

sodium hydrogen carbonate

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

sodium acetate

bromine

→

subtitled compound

Ausbeute 105.0%

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

Ausbeute 105.0%

Lösungsmittel

acetic acid

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with EtOAc (×2)
2. 2
   Waschenthe combined organic layers were washed with water, sat. sodium hydrogen carbonate solution, water
3. 3
   Trocknendried (MgSO4)
4. 4
   Sonstigeevaporated

Vorschrift

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).

Quelle