تفاعل #66261

معادلة التفاعل

Na2CO3

4-bromo-2-nitrobenzaldehyde

4-(pyrrolidine-1-carbonyl)phenylboronic acid

EtOH

→

3-nitro-4′-(pyrrolidine-1-carbonyl)biphenyl-4-carbaldehyde

المردود 178.9%

المذيبات

toluene

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe reaction mixture was cooled to room temperature
2. 2
   أخرىthe organic layer was separated
3. 3
   استخلاصThe aqueous layer was extracted with EtOAc (300 mL)
4. 4
   غسيلThe combined organic layers were washed with brine (500 mL)
5. 5
   تجفيفdried over MgSO4
6. 6
   ترشيحfiltered
7. 7
   تركيزconcentrated under reduced pressure
8. 8
   أخرىto give the crude material that
9. 9
   أخرىobtained from an additional run in the same reaction scale
10. 10
    أخرىwas purified by silica gel flash column chromatography (CH2Cl2 to 1% MeOH in CH2Cl2)

الإجراء التجريبي

To a solution of 4-bromo-2-nitrobenzaldehyde (20.2 g, 87.9 mmol), 4-(pyrrolidine-1-carbonyl)phenylboronic acid (21.2 g, 96.7 mmol), and Pd(PPh3)4 (508 mg, 0.440 mmol) in toluene (200 mL) was added EtOH (40 mL) followed by Na2CO3 (70.0 mL, 140 mmol, 2 M aq solution) at room temperature. The resulting mixture was heated at 100° C. for 18 h. The reaction mixture was cooled to room temperature and the organic layer was separated. The aqueous layer was extracted with EtOAc (300 mL). The combined organic layers were washed with brine (500 mL), dried over MgSO4, filtered, and concentrated under reduced pressure to give the crude material that was combined with another batch of the crude material obtained from an additional run in the same reaction scale. The combined crude material was purified by silica gel flash column chromatography (CH2Cl2 to 1% MeOH in CH2Cl2) to afford 51 g (90%) of 3-nitro-4′-(pyrrolidine-1-carbonyl)biphenyl-4-carbaldehyde.

المصدر