Hexane → 2-(2-nitrophenyl)thiophene

HRID 1983872Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1983872
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1B(O)O.I[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N+:16]([O-:18])=[O:17].C([O-])([O-])=O.[K+].[K+].CCCCCC>COCCOC.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+:16]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)([O-:18])=[O:17]

Komponenten

7

Edukt 4

HCID 8058HexaneHCID 11430Potassium CarbonateHCID 69115o-IodonitrobenzeneHCID 27339602-Thiopheneboronic acid

Produkt 1

HCID 91672612-(2-nitrophenyl)thiopheneAusbeute 107,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

14.07 g (110 mmol) of 2-thiophene-boronic acid, 24.9 g (100 mmol) of 1-iodo-2-nitrobenzene, and 5.78 g (5 mmol) of tetrakis(triphenylphosphine)palladium(0) were dissolved in 250 ml of ethylene glycol dimethyl ether (DME), and 70 ml of 2M K2CO3 aqueous solution was added to the solution, and then the mixture was refluxed at 80° C. for 12 hours. After the reaction was completed, an organic layer was isolated and concentrated, and then isolated by column chromatography using hexane, thereby obtaining 22.1 g (yield: 98%) of 2-(2′-nitrophenyl)-thiophene (A′).

Aufarbeitung

  1. customan organic layer was isolated
  2. concentrationconcentrated
  3. customisolated by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-9694b2f7e6304b59a02c513545c1e0f3
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07541736B2

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