Reaktion #76328

Reaktionsgleichung

toluene

3-bromofuran

3-formylphenylboronic acid

K2CO3

→

3-(3-furanyl)benzaldehyde

Ausbeute 10.0%

Lösungsmittel

water

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe slurry was heated
2. 2
   Temperaturto reflux under argon for 2 h
3. 3
   Extraktionextracted with ethyl acetate
4. 4
   WaschenThe organic layer was washed with brine
5. 5
   Trocknendried (MgSO4)
6. 6
   Sonstigeevaporated to an oil
7. 7
   SonstigePurification by flash chromatography on silica gel eluting with 5% ethyl acetate in hexane

Vorschrift

Ex-601A) To a toluene (10 mL) solution of 3-bromofuran (0.54 mL, 6.0 mmol) was added 3-formylphenylboronic acid (1.00 g, 6.7 mmol) and DMF (4 mL). To the resulting solution was added K2CO3 (1.85 g, 13.4 mmol) and Pd(PPh3)4 (0.40 g, 0.35 mmol). The slurry was heated to reflux under argon for 2 h. The cooled mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried (MgSO4) and evaporated to an oil. Purification by flash chromatography on silica gel eluting with 5% ethyl acetate in hexane gave 0.10 g (10%) of the desired 3-(3-furanyl)benzaldehyde product as a yellow oil. MS: m/z=173.0 [M+H]+.

Quelle