Reaktion #9419

Reaktionsgleichung

sodium carbonate

3,3-dimethyl-indol-2-one

sodium acetate

bromine

→

subtitled compound

Ausbeute 92.0%

5-bromo-1,3-dihydro-3,3-dimethyl-2H-indol-2-one

Ausbeute 92.0%

Lösungsmittel

acetic acid

water

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with ethyl acetate (×3)
2. 2
   Trocknendried (MgSO4)
3. 3
   Filtrationfiltered
4. 4
   Sonstigeevaporated

Vorschrift

3,3-dimethyl-indol-2-one (0.65 g, 4.03 mmol) and sodium acetate (0.33 g, 4.07 mmol) were stirred in acetic acid (5 cm3) then bromine (0.66 g, 4.13 mmol) in acetic acid (5 cm3) was added drop-wise to the reaction mixture. The reaction was stirred for 50 min., then poured into water. The mixture was basified with sodium carbonate, extracted with ethyl acetate (×3), dried (MgSO4), filtered, and evaporated to give the subtitled compound (0.89 g, 92%) 1H NMR (DMSO-d6) δ 1.21 (s, 6 H), 6.76 (d, 1 H, J=8.22 Hz), 7.29 (dd, 1 H, J=2.12 Hz, 8.23 Hz), 7.49 (d, 1 H, J=2.03 Hz), 10.4 (s, 1H).

Quelle