Réaction #59115

Équation de réaction

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

Rendement 75.2%

Solvants

dioxane

Conditions de réaction

Traitement

1. 1
   Autrethe mixture was thoroughly degassed
2. 2
   Températurewas cooled to rt
3. 3
   workup.ADDITIONWater was added
4. 4
   Extractionthe mixture was extracted twice with ethyl acetate
5. 5
   SéchageThe combined extracts were dried over anhydrous sodium sulfate
6. 6
   Concentrationconcentrated under reduced pressure
7. 7
   AutreThe residue was purified by flash chromatography (Biotage flash 75, 5:1 ethyl acetate/hexane)

Mode opératoire

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).

Source