Reaktion #1804832

Reaktionsgleichung

1-(4-Bromo-2-hydroxy-phenyl)-ethanone

2-chloro-1-(2,4-dichlorophenyl)ethanone

K2CO3

ethyl acetate

→

desired compound

Ausbeute 44.1%

(6-Bromo-3-methyl-benzofuran-2-yl)(2,4-dichloro-phenyl)methanone

Ausbeute 44.1%

Lösungsmittel

N,N-dimethylformamide

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturafter cooled down to rt
2. 2
   ExtraktionExtracted with ethyl acetate (3×50 mL)
3. 3
   TrocknenThe organic layer was dried (Na2SO4)
4. 4
   Filtrationfiltered
5. 5
   Sonstigeevaporated in vacuo
6. 6
   WaschenThe crude product was washed by hexane (2×30 mL)

Vorschrift

To a stirred solution of 1-(4-Bromo-2-hydroxy-phenyl)-ethanone (2.81 g, 13.1 mmol, from step 1) and 2-chloro-1-(2,4-dichlorophenyl)ethanone (6.88 g, 30.8 mmol, 2.3 eq) in anhydrous N,N-dimethylformamide (50 mL) was added K2CO3 (7.42 g, 53.7 mmol, 4.0 eq). The dark brown reaction mixture was stirred at 90° C. for 38 h. The reaction was poured into ethyl acetate (100 mL) and water (100 mL) after cooled down to rt. Extracted with ethyl acetate (3×50 mL). The organic layer was dried (Na2SO4), filtered, and evaporated in vacuo. The crude product was washed by hexane (2×30 mL) followed by ethyl ether (2×30 mL) to provide 2.22 g (44%) of the desired compound as light yellow solid. 1H-NMR (CDCl3) δ 7.64 (d, J=1.9 Hz, 1H), 7.54 (d, J=8.7 Hz, 1H), 7.49 (d, J=1.9 Hz, 1H), 7.45-7.36 (m, 3H), 2.57 (s, 3H); MS LC-MS (MH+=385).

Quelle