Reaktion #676024

Reaktionsgleichung

2,2′,5′-trichloro-4-methoxy-5-vinylbiphenyl

water

→

desired product

Ausbeute 29.0%

2-(2′,5′,6-Trichloro-4-methoxybiphenyl-3-yl)acetaldehyde

Ausbeute 29.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   workup.STIRRINGthe resulting mixture was stirred at room temperature for another 6 h
3. 3
   SonstigeThe mixture was partitioned between ethyl acetate and water
4. 4
   WaschenThe organic layer was washed with water
5. 5
   Trocknendried over anhydrous Na2SO4
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated in vacuo
8. 8
   SonstigeThe residue was purified by flash column chromatography on silica gel (1-3% ethyl acetate/petroleum ether)

Vorschrift

To a mixture of 2,2′,5′-trichloro-4-methoxy-5-vinylbiphenyl (1.0 g, 3.2 mmol) in anhydrous DMF (10 mL), PdCl2 (1.14 g, 6.4 mmol) was added and the resulting mixture was stirred at room temperature under nitrogen for 16 h. To this mixture, water (0.5 mL) was added and the resulting mixture was stirred at room temperature for another 6 h. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with water, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (1-3% ethyl acetate/petroleum ether) to afford the desired product (300 mg, 29% yield) as a white solid.

Quelle