Water → HCID 59456318, Verbindung

HRID 1873405

Reaktionsgleichung

Reaktionsgleichung von HRID 1873405
Br[C:2]1[Se:3][CH:4]=[CH:5][CH:6]=1.[CH2:7]([C:10]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][CH:11]=1)[CH2:8][CH3:9].C(=O)([O-])[O-].[Na+].[Na+].O>C1(C)C=CC=CC=1.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>[CH2:7]([C:10]1[CH:15]=[CH:14][C:13]([C:2]2[Se:3][CH:4]=[CH:5][CH:6]=2)=[CH:12][CH:11]=1)[CH2:8][CH3:9]

Komponenten

7

Edukt 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 1370132-BromoselenopheneHCID 4100861(4-Propylphenyl)boronic acid

Produkt 1

HCID 59456318HCID 59456318, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 21863594Toluene ethanolLösungsmittel

Versuchsvorschrift

A mixture of 26.0 g (0.12 mol) of 2-bromoselenophene, 20.5 g (0.13 mol) of 4-propylphenylboronic acid, 7.0 g (6.1 mmol) of tetrakis-(triphenylphosphine)palladium(0) and 140 ml of 2 N sodium carbonate soln. in 300 ml of toluene/ethanol (1:1) is heated under reflux for 20 h. A further 7.0 g (6.06 mmol) of tetrakis(triphenylphosphine)palladium(0) are added, and the mixture is refluxed again for 3 h. After cooling, water is added, and the organic phase is separated off. The aqueous phase is extracted with toluene, and the combined organic phases are washed with water and sat. sodium chloride soln. The solution is dried using sodium sulfate and concentrated to dryness. The residue is purified by column chromatography (SiO2, n-heptane). 2-(4-Propylphenyl)selenophene is obtained as a yellow liquid.

Aufarbeitung

  1. temperatureunder reflux for 20 h
  2. temperaturethe mixture is refluxed again for 3 h
  3. temperatureAfter cooling
  4. customthe organic phase is separated off
  5. extractionThe aqueous phase is extracted with toluene
  6. washthe combined organic phases are washed with water and sat. sodium chloride soln
  7. customThe solution is dried
  8. concentrationconcentrated to dryness
  9. customThe residue is purified by column chromatography (SiO2, n-heptane)

Quellen und Nachweise

ORD-Eintrag
ord-a75389601c804176925a13fc513e3467
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304036B2

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