Reaktion #7094

Reaktionsgleichung

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

sodium acetate

bromine

→

subtitled compound

Ausbeute 67.0%

5′-Bromospiro[cyclohexane-1,3′-[3H]indol]-2′(1′H)-one

Ausbeute 67.0%

Lösungsmittel

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe reaction mixture was partitioned between water and EtOAc
2. 2
   ExtraktionThe aqueous phase was extracted twice with EtOAc
3. 3
   WaschenThe combined organic layers were washed with water
4. 4
   Trocknendried (MgSO4)
5. 5
   Sonstigeevaporated
6. 6
   Sonstigethe residue was triturated with hexane
7. 7
   SonstigeThe precipitate was collected
8. 8
   Sonstigedried in vacuo

Vorschrift

To a solution of spiro[cyclohexane-1,3′-[3H]indol]-2′(1′H)-one (17.6 g, 0.09 mol) in acetic acid (300 cm3) was added sodium acetate (8.0 g, 0.1 mol) and bromine (14.6 g, 0.091 mol) with stirring. After 30 min. at room temperature, the reaction mixture was partitioned between water and EtOAc. The aqueous phase was extracted twice with EtOAc. The combined organic layers were washed with water, dried (MgSO4) and evaporated and the residue was triturated with hexane. The precipitate was collected, and dried in vacuo to obtain the subtitled compound (16.5 g, 67%) as off-white crystals: mp 196–199° C.; 1H NMR (DMSO-d6) δ 1.62 (m, 10H), 6.8 (d, 1H, J=6.8 Hz), 7.36 (d, 1H, J=8.2, 1.8 Hz), 7.58 (dd, 1H, J=8.2, 1.8 Hz), 10.44 (s, 1H).

Quelle