Sodium Carbonate → HCID 59450506, Verbindung

HRID 72300

Reaktionsgleichung

Reaktionsgleichung von HRID 72300
[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1B(O)O.Br[C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH3:20])=[C:15]([N+:21]([O-:23])=[O:22])[CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.C(OCC)(=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>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]([C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH3:20])=[C:15]([N+:21]([O-:23])=[O:22])[CH:14]=2)=[C:2]([F:1])[CH:7]=1

Komponenten

8

Edukt 3

HCID 10340Sodium CarbonateHCID 4193595(4-Chloro-2-fluorophenyl)boronic acidHCID 75669964-Bromo-1-ethyl-2-nitrobenzene

Produkt 1

HCID 59450506HCID 59450506, VerbindungAusbeute 98,4 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Tetrakis(triphenylphosphine)palladium(0) is added to a solution of 2-fluoro-4-chlorophenylboronic acid (1.25 g, 7.17 mmol) and 4-bromo-1-ethyl-2-nitrobenzene (1.50 g, 6.52 mmol) in 1,2-dimethoxyethane (12 ml) and the mixture is stirred at room temperature for 15 minutes. A solution of sodium carbonate (5.52 g, 52 mmol) in water (26 ml) is added and the mixture is heated to reflux for 17 hours. The reaction mixture is cooled to room temperature, diluted with ethyl acetate and the two phases separated. The organic phase is collected, the aqueous phase is extracted with ethyl acetate and the organic solutions are combined, dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated under reduced pressure to give 4′-chloro-4-ethyl-2′-fluoro-3-nitrobiphenyl (1.795 g), used without further purification in the next step.

Aufarbeitung

  1. temperaturethe mixture is heated
  2. temperatureto reflux for 17 hours
  3. temperatureThe reaction mixture is cooled to room temperature
  4. customthe two phases separated
  5. customThe organic phase is collected
  6. extractionthe aqueous phase is extracted with ethyl acetate
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customthe filtrate is evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-614993ffde28407cb8fb564fd5ea12dd
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08828908B2

Verknüpfte Notizen

Wird geladen…