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Sodium Carbonate → 3'-Nitro-2'-methoxy-biphenyl-4-carbaldehyde

HRID 384357
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 384357
O1CCOCC1.[CH:7]([C:9]1[CH:14]=[CH:13][C:12](B(O)O)=[CH:11][CH:10]=1)=[O:8].Br[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[C:20]=1[O:28][CH3:29].C(=O)([O-])[O-].[Na+].[Na+]>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.O>[N+:25]([C:21]1[C:20]([O:28][CH3:29])=[C:19]([C:12]2[CH:13]=[CH:14][C:9]([CH:7]=[O:8])=[CH:10][CH:11]=2)[CH:24]=[CH:23][CH:22]=1)([O-:27])=[O:26]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 5910734-Formylphenylboronic AcidHCID 225057131-Bromo-2-methoxy-3-nitrobenzene

Produkt 1

HCID 574838283'-Nitro-2'-methoxy-biphenyl-4-carbaldehydeAusbeute 80,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 60 mL of 1,4-dioxane and 10 mL of water was added 4-formylphenylboronic acid (3.0 g, 0.02 mol), followed by 1-bromo-2-methoxy-3-nitro-benzene 1c (4.64 g, 0.02 mol), tetrakis(triphenylphosphine)palladium (1.15 g, 1 mmol) and sodium carbonate (4.24 g, 0.04 mol). Upon completion of the addition, the mixture was heated to reflux for 5 hours. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was filtered and the filter cake was washed with ethyl acetate. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography to obtain the title compound 3′-nitro-2′-methoxy-biphenyl-4-carbaldehyde 32a (4.1 g, 80.4%) as a yellow solid.

Aufarbeitung

  1. additionUpon completion of the addition
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 5 hours
  4. filtrationThe mixture was filtered
  5. washthe filter cake was washed with ethyl acetate
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-3c126ed7984b4484b843fe918a9f3b9d
Quelldatensatz
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08367710B2

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