تفاعل #59115

معادلة التفاعل

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

المردود 75.2%

المذيبات

dioxane

ظروف التفاعل

المعالجة

1. 1
   أخرىthe mixture was thoroughly degassed
2. 2
   درجة الحرارةwas cooled to rt
3. 3
   workup.ADDITIONWater was added
4. 4
   استخلاصthe mixture was extracted twice with ethyl acetate
5. 5
   تجفيفThe combined extracts were dried over anhydrous sodium sulfate
6. 6
   تركيزconcentrated under reduced pressure
7. 7
   أخرىThe residue was purified by flash chromatography (Biotage flash 75, 5:1 ethyl acetate/hexane)

الإجراء التجريبي

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).

المصدر