Sodium Carbonate → HCID 59456349, Verbindung

HRID 1873409

Reaktionsgleichung

Reaktionsgleichung von HRID 1873409
Br[C:2]1[Se:3][CH:4]=[CH:5][CH:6]=1.[CH2:7]([CH:9]1[CH2:14][CH2:13][CH:12]([C:15]2[CH:20]=[CH:19][C:18](B(O)O)=[C:17]([F:24])[C:16]=2[F:25])[CH2:11][CH2:10]1)[CH3:8].C(=O)([O-])[O-].[Na+].[Na+]>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]([CH:9]1[CH2:10][CH2:11][CH:12]([C:15]2[CH:20]=[CH:19][C:18]([C:2]3[Se:3][CH:4]=[CH:5][CH:6]=3)=[C:17]([F:24])[C:16]=2[F:25])[CH2:13][CH2:14]1)[CH3:8]

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 1370132-BromoselenopheneHCID 59456333HCID 59456333, Verbindung

Produkt 1

HCID 59456349HCID 59456349, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 21863594Toluene ethanolLösungsmittel

Versuchsvorschrift

A mixture of 8.9 g (42.4 mmol) of 2-bromoselenophene, 16.0 g (59.7 mmol) of 4-(4-ethylcyclohexyl)-2,3-difluorophenylboronic acid, 3.93 g (3.40 mmol) of tetrakis(triphenylphosphine)palladium(0) and 125 ml of 2 N sodium carbonate soln. in 600 ml of toluene/ethanol (1:1) is heated under reflux for 20 h. After cooling, the organic phase is separated off, and the aqueous phase is extracted with toluene. The combined organic phases are washed with sat. sodium chloride soln., and the solution is dried using sodium sulfate. The solution is concentrated to dryness, and the residue is purified by column chromatography (SiO2, toluene). The further purification is carried out by recrystallisation from n-heptane:EtOH=1:1 and IPA. 2-[4-(4-Ethylcyclohexyl)-2,3-difluorophenyl]selenophene is obtained as a pale-yellowish solid.

Aufarbeitung

  1. temperatureunder reflux for 20 h
  2. temperatureAfter cooling
  3. customthe organic phase is separated off
  4. extractionthe aqueous phase is extracted with toluene
  5. washThe combined organic phases are washed with sat. sodium chloride soln
  6. custom, and the solution is dried
  7. concentrationThe solution is concentrated to dryness
  8. customthe residue is purified by column chromatography (SiO2, toluene)
  9. customThe further purification
  10. customis carried out by recrystallisation from n-heptane

Quellen und Nachweise

ORD-Eintrag
ord-9141115f49904b5e9db82f30946f0890
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304036B2

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