Sodium Carbonate → HCID 59456334, Verbindung

HRID 1873427

Reaktionsgleichung

Reaktionsgleichung von HRID 1873427
Br[C:2]1[Se:3][CH:4]=[CH:5][CH:6]=1.[F:7][C:8]1[CH:9]=[C:10]([C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH3:24])=[CH:19][CH:18]=2)[CH:11]=[CH:12][C:13]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C>[CH2:23]([C:20]1[CH:19]=[CH:18][C:17]([C:10]2[CH:11]=[CH:12][C:13]([C:2]3[Se:3][CH:4]=[CH:5][CH:6]=3)=[C:8]([F:7])[CH:9]=2)=[CH:22][CH:21]=1)[CH3:24]

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 1370132-BromoselenopheneHCID 534025754'-Ethyl-3-fluorobiphenyl-4-boronic acid

Produkt 1

HCID 59456334HCID 59456334, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21863594Toluene ethanolLösungsmittel

Versuchsvorschrift

A mixture of 34.2 g (0.16 mol) of 2-bromoselenophene, 40.0 g (0.16 mol) of 3-fluoro-4′-ethylbiphenyl-4-ylboronic acid, 10.0 g (8.65 mmol) of tetrakis-(triphenylphosphine)palladium(0) and 200 ml of 2 N sodium carbonate soln. in 500 ml of toluene/ethanol (2:3) is heated at 90° C. for 2 h. After cooling, the organic phase is separated off, and the aqueous phase is extracted with toluene. The combined organic phases are washed with water, and the solution is dried using sodium sulfate. The solution is concentrated to dryness, and the residue is purified by column chromatography (SiO2, n-heptane:toluene=9:1). 2-(4′-Ethyl-3-fluorobiphenyl-4-yl)-selenophene is obtained as a yellow solid.

Aufarbeitung

  1. temperatureAfter cooling
  2. customthe organic phase is separated off
  3. extractionthe aqueous phase is extracted with toluene
  4. washThe combined organic phases are washed with water
  5. customthe solution is dried
  6. concentrationThe solution is concentrated to dryness
  7. customthe residue is purified by column chromatography (SiO2, n-heptane:toluene=9:1)

Quellen und Nachweise

ORD-Eintrag
ord-b74f375a4d89404897a55cbadbb82001
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304036B2

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