反応 #9621

反応方程式

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

収率 75.2%

溶媒

dioxane

反応条件

後処理

1. 1
   その他the mixture was thoroughly degassed
2. 2
   温度was cooled to rt
3. 3
   workup.ADDITIONWater was added
4. 4
   抽出the mixture was extracted twice with ethyl acetate
5. 5
   乾燥The combined extracts were dried over anhydrous sodium sulfate
6. 6
   濃縮concentrated under reduced pressure
7. 7
   その他The residue was purified by flash chromatography (Biotage flash 75, 5:1 ethyl acetate/hexane)

実験手順

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).

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