Reaktion #7077

Reaktionsgleichung

sodium carbonate

bromine

3-methyl-2-indolinone

sodium acetate

→

title compound

Ausbeute 93.7%

5-bromo-3-methyl-indol-2-one

Ausbeute 93.7%

Lösungsmittel

acetic acid

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto quench
2. 2
   Sonstigethe reaction
3. 3
   ExtraktionThe water layer was extracted with EtOAc (×3)
4. 4
   Trocknendried (MgSO4)
5. 5
   Filtrationfiltered
6. 6
   Sonstigeevaporated

Vorschrift

Under an atmosphere of nitrogen, bromine (0.96 g, 6.0 mmol) in acetic acid (5 cm3) was added drop wise to a solution of 3-methyl-2-indolinone (0.8749 g, 6.0 mmol) (Kende, et al, Synth. Commun., 12, 1, 1982) and sodium acetate (0.50 g, 6.0 mmol) in acetic acid (10 cm3). The reaction was stirred at room temperature for 3.5 h. Saturated sodium carbonate was added to quench the reaction. The water layer was extracted with EtOAc (×3), dried (MgSO4), filtered, and evaporated to give the title compound (1.26 g, 93%), Mp=119–120° C.; 1H NMR (DMSO) δ 1.32 (d, 3H, J=7.66 Hz), 3.45 (q, 1H, J=7.62 Hz), 6.77 (d, 1H, J=8.23 Hz), 7.46 (s, 1H), 7.36–7.33 (m, 1H), 10.4 (s, 1H); IR (KBr) 3200, 1725 cm−1; MS (EI) m/z 224/226 (M−H)−; CHN calculated for C9H8BrNO: C, 47.82; H, 3.57; N, 6.20; Found: C, 47.44; H, 3.42; N, 6.04.

Quelle