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Ethanol → 2-Nitro-3-(4-tolyl)thiophene

HRID 1289072
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1289072
Br[C:2]1[CH:6]=[CH:5][S:4][C:3]=1[N+:7]([O-:9])=[O:8].[C:10]1([CH3:20])[CH:15]=[CH:14][C:13](OB(O)O)=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+].C(O)C>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.C1(C)C=CC=CC=1>[N+:7]([C:3]1[S:4][CH:5]=[CH:6][C:2]=1[C:13]1[CH:14]=[CH:15][C:10]([CH3:20])=[CH:11][CH:12]=1)([O-:9])=[O:8]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 12014963-Bromo-2-nitrothiopheneHCID 190353504-Methylphenyl dihydrogen borate

Produkt 1

HCID 189253902-Nitro-3-(4-tolyl)thiopheneAusbeute 74,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 0.8 g of 3-bromo-2-nitrothiophene, 0.52 g of 4-tolylboric acid, 5 ml of a 2M-aqueous potassium carbonate solution, 2.5 ml of ethanol and 30 ml of toluene was stirred at room temperature for 30 minutes in a nitrogen atmosphere. Successively 0.15 g of Pd(PPh3)4 was added and refluxed by heating for 7 hours. After separating into two layers, the organic layer was washed with water and dried over anhydrous sodium sulfate. Solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 0.56 g (70% yield) of the product as a yellow crystal. 1H-NMR(CDCl3, δ value):2.42(3H, s), 7.01(1H, d, J=5.1), 7.25(2H, d, J=8.1), 7.37(2H, d, J=8.1), 7.47(1H, d, J=5.1)

Aufarbeitung

  1. temperaturerefluxed
  2. temperatureby heating for 7 hours
  3. customAfter separating into two layers
  4. washthe organic layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationSolvent was distilled off under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-55cbc03ad7d54fa993c4316081d4f1f8
Quelldatensatz
uspto-grants-1998_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05747518

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