Sodium Carbonate → 4-Selenophen-2-ylphenol

HRID 1873423

Reaktionsgleichung

Reaktionsgleichung von HRID 1873423
I[C:2]1[Se:3][CH:4]=[CH:5][CH:6]=1.[OH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.CC(OC)(C)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>[Se:3]1[CH:4]=[CH:5][CH:6]=[C:2]1[C:11]1[CH:12]=[CH:13][C:8]([OH:7])=[CH:9][CH:10]=1

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 1421832-IodoselenopheneHCID 2773454(2-Hydroxyphenyl)boronic acid

Produkt 1

HCID 126128064-Selenophen-2-ylphenol

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 15413tert-Butyl methyl etherLösungsmittelHCID 21863594Toluene ethanolLösungsmittel

Versuchsvorschrift

A mixture of 27.9 g (0.11 mol) of 2-iodoselenophene, 15.0 g (0.11 mol) of 2-hydroxyphenylboronic acid, 6.8 g (5.88 mmol) of tetrakis(triphenylphosphine)palladium(0) and 235 ml of 2 N sodium carbonate soln. in 600 ml of toluene/ethanol (1:1) is heated under reflux for 19 h. The mixture is diluted with MTBE and washed with water. The aqueous phase is extracted with MTBE, and the combined organic phases are washed with 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:MTBE=4:1→1:1). Further purification is carried out by digestion in cold n-heptane; 4-selenophen-2-ylphenol is obtained as a beige solid.

Aufarbeitung

  1. temperatureunder reflux for 19 h
  2. washwashed with water
  3. extractionThe aqueous phase is extracted with MTBE
  4. washthe combined organic phases are washed with sat. sodium chloride soln
  5. customThe solution is dried
  6. concentrationconcentrated to dryness
  7. customThe residue is purified by column chromatography (SiO2, n-heptane:MTBE=4:1→1:1)
  8. customFurther purification

Quellen und Nachweise

ORD-Eintrag
ord-0758f29e362d49169dbb883bb272b792
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304036B2

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