Reacción #9621

Ecuación de reacción

Toluene

sodium carbonate

Ethyl 4-(4-bromophenyl)-4-oxo-2-(2-phenylethyl)butanoate

4-nitrophenylboronic acid

→

ethyl 4-(4′-nitro-1,1′-biphenyl-4-yl)-4-oxo-2-(2-phenylethyl)butanoate

Rendimiento 75.2%

Disolventes

dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe mixture was thoroughly degassed
2. 2
   Temperaturawas cooled to rt
3. 3
   workup.ADDITIONWater was added
4. 4
   Extracciónthe mixture was extracted twice with ethyl acetate
5. 5
   SecadoThe combined extracts were dried over anhydrous sodium sulfate
6. 6
   Concentraciónconcentrated under reduced pressure
7. 7
   OtroThe residue was purified by flash chromatography (Biotage flash 75, 5:1 ethyl acetate/hexane)

Procedimiento

Ethyl 4-(4-bromophenyl)-4-oxo-2-(2-phenylethyl)butanoate (4.32 g, 11.1 mmol) and 4-nitrophenylboronic acid (2.22, 13.3 mmol) was added to a dry flask under argon. Toluene (100 mL), dioxane (25 mL), saturated aqueous sodium carbonate (30 mL), and [1,1′-bis(diphenyl-phosphino)-ferrocene]dichloro palladium(II) (1:1 complex with dichloromethane, 453 mg, 0.55 mmol) were added and the mixture was thoroughly degassed. The resulting mixture was then heated at 85° C. for 16 h before it was cooled to rt. Water was added and the mixture was extracted twice with ethyl acetate. The combined extracts were dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography (Biotage flash 75, 5:1 ethyl acetate/hexane) to afford ethyl 4-(4′-nitro-1,1′-biphenyl-4-yl)-4-oxo-2-(2-phenylethyl)butanoate (3.6 g, 75%). HPLC ret. time 3.99 min, 1H NMR (300 MHz, CDCl3) δ 1.29 (t, 3H), 1.85–2.08 (m, 2H), 2.71 (t, 2H), 3.05–3.20 (m, 2H), 3.45–3.52 (m, 1H), 4.20 (q, 2H), 7.18–7.31 (m, 5H), 7.72 (d, 2H), 7.78 (d, 2H), 8.05 (d, 2H), 8.33 (d, 2H).

Fuente