Sodium Carbonate → HCID 86644413, Verbindung

HRID 2194693Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2194693
Br[C:2]1[CH:3]=[C:4]([CH:8]=O)[S:5][C:6]=1Br.[F:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1B(O)O.[C:20](=[O:23])([O-])[O-].[Na+].[Na+]>COCCOC.O.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:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:3]1[CH:2]=[C:6]([CH:20]=[O:23])[S:5][C:4]=1[C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[F:10]

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 8131644,5-Dibromothiophene-2-carbaldehydeHCID 27343542-Fluorophenylboronic acid

Produkt 1

HCID 86644413HCID 86644413, VerbindungAusbeute 14 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittel2×HCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A suspension of 4,5-dibromothiophene-2-carbaldehyde (2.0 g), (2-fluorophenyl)boronic acid (1.6 g), tetrakis(triphenylphosphine)palladium (0) (855 mg) and sodium carbonate (2.0 g) in 1,2-dimethoxyethane (32 mL) and water (8 mL) was stirred at 80° C. for 6 hr under a nitrogen atmosphere. The reaction mixture was cooled to room temperature, water was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=99:1→9:1→17:3) to give the title compound as a colorless amorphous (yield 310 mg, yield 14%).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=99:1→9:1→17:3)

Quellen und Nachweise

ORD-Eintrag
ord-8490dc657c274b36b0c91e3bb6ac5c8d
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08334301B2

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