Ethanol → 3-Nitro-4'-(pyrrolidine-1-carbonyl)biphenyl-4-carbaldehyde

HRID 593424

Reaktionsgleichung

Reaktionsgleichung von HRID 593424
Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.[N:13]1([C:18]([C:20]2[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=2)=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14]1.CCO.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N+:10]([C:4]1[CH:3]=[C:2]([C:23]2[CH:22]=[CH:21][C:20]([C:18]([N:13]3[CH2:14][CH2:15][CH2:16][CH2:17]3)=[O:19])=[CH:25][CH:24]=2)[CH:9]=[CH:8][C:5]=1[CH:6]=[O:7])([O-:12])=[O:11]

Komponenten

7

Edukt 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 6080994-Bromo-2-nitrobenzaldehydeHCID 2773571(4-(Pyrrolidine-1-carbonyl)phenyl)boronic acid

Produkt 1

HCID 866526783-Nitro-4'-(pyrrolidine-1-carbonyl)biphenyl-4-carbaldehydeAusbeute 178,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

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.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe organic layer was separated
  3. extractionThe aqueous layer was extracted with EtOAc (300 mL)
  4. washThe combined organic layers were washed with brine (500 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give the crude material that
  9. customobtained from an additional run in the same reaction scale
  10. customwas purified by silica gel flash column chromatography (CH2Cl2 to 1% MeOH in CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-d2670b63e4fb4548944742c01ded3312
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242964B2

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