Reaktion #10714

Reaktionsgleichung

water

Benzo[b]thiophene-2-boronic acid

sodium carbonate

5-bromo-2,4-dimethoxybenzaldehyde

→

5-(benzo[b]thien-2-yl)-2,4-dimethoxybenzaldehyde

Ausbeute 83.0%

Lösungsmittel

ethylene glycol dimethyl ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe mixture was stirred
2. 2
   Temperaturat reflux under nitrogen for 24 hours
3. 3
   TemperaturUpon cooling to room temperature
4. 4
   Extraktionextracted with ethyl acetate
5. 5
   TrocknenThe organic phase was dried over sodium sulfate
6. 6
   Sonstigeevaporated

Vorschrift

Ex-3A: A sample of 5-bromo-2,4-dimethoxybenzaldehyde (4.9 g, 20.0 mmol) was dissolved in ethylene glycol dimethyl ether (50 mL). Tetrakis(triphenylphosphine)palladium(0) (2.32 g, 2 mmol) was added, and the mixture was stirred at room temperature under nitrogen for 5 min. Benzo[b]thiophene-2-boronic acid (4.27 g, 24 mmol) and sodium carbonate solution (2 M, 20 mL) were added. The mixture was stirred at reflux under nitrogen for 24 hours. Upon cooling to room temperature, the mixture was poured into water and extracted with ethyl acetate. The organic phase was dried over sodium sulfate and evaporated. Silica gel chromatography (hexane/ethyl acetate 2:1 then 1:1) gave 4.75 g (83%) of the desired 5-(benzo[b]thien-2-yl)-2,4-dimethoxybenzaldehyde. 1H NMR (CDCl3) δ 10.36 (s, 1H), 8.20 (s, 1H), 7.83–7.78 (m, 2H), 7.68 (s, 1H), 7.36–7.27 (m, 2H), 6.54 (s, 1H), 4.06 (s, 3H), 4.00 (s, 3H).

Quelle