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Sodium Bicarbonate → HCID 58028448, Verbindung

HRID 1399416
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1399416
[Na+].[CH2:2]([C:8]1[S:12][C:11](OB(O)[O-])=[CH:10][CH:9]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].Br[C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:26][CH:25]=2)=[C:20]([F:35])[CH:19]=1.C(=O)([O-])O.[Na+]>C1COCC1.O.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>[F:35][C:20]1[CH:19]=[C:18]([C:11]2[S:12][C:8]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])=[CH:9][CH:10]=2)[CH:23]=[CH:22][C:21]=1[C:24]1[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:26][CH:25]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 516892Sodium BicarbonateHCID 227175154-Bromo-2-fluoro-4'-pentyl-1,1'-biphenylHCID 131730280HCID 131730280, Verbindung

Produkt 1

HCID 58028448HCID 58028448, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysator
HCID 15413
tert-Butyl methyl ether
Lösungsmittel
HCID 21881883Oxolane--water (1/1)Lösungsmittel

Versuchsvorschrift

A mixture of 3.30 g (13.1 mmol) of 5-hexylthiophen-2-ylhydroxyboronic acid sodium salt, 4.20 g (13.1 mmol) of 4-bromo-2-fluoro-4′-pentylbiphenyl, 2.2 g (26.2 mmol) of sodium hydrogencarbonate and 0.70 g (0.61 mmol) of tetrakis(triphenylphosphine)palladium(0) in THF/water (1:1) is heated under reflux for 6 h. The mixture is diluted with MTBE, and the organic phase is separated off. The aqueous phase is extracted with MTBE. The combined organic phases are washed with sat. sodium chloride solution and dried using sodium sulfate. The solution is evaporated to dryness, and the residue is purified by column chromatography (SiO2, n-heptane). The further purification is carried out by recrystallisation from methanol/pentane (5:1), giving 2-(2-fluoro-4′-pentylbiphenyl-4-yl)-5-hexylthiophene as a colourless solid having an m.p. of 44° C.

Aufarbeitung

  1. temperatureis heated
  2. temperatureunder reflux for 6 h
  3. customthe organic phase is separated off
  4. extractionThe aqueous phase is extracted with MTBE
  5. washThe combined organic phases are washed with sat. sodium chloride solution
  6. customdried
  7. customThe solution is evaporated to dryness
  8. customthe residue is purified by column chromatography (SiO2, n-heptane)
  9. customThe further purification
  10. customis carried out by recrystallisation from methanol/pentane (5:1)

Quellen und Nachweise

ORD-Eintrag
ord-8c4d01e596614ee5ab4d9234423106b9
Quelldatensatz
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08906261B2

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