Potassium Carbonate → N-(4'-chloro-3-ethylbiphen-4-yl)acetamide

HRID 72288

Reaktionsgleichung

Reaktionsgleichung von HRID 72288
Br[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[C:4]([CH2:12][CH3:13])[CH:3]=1.[Cl:14][C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>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>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([C:2]2[CH:3]=[C:4]([CH2:12][CH3:13])[C:5]([NH:8][C:9](=[O:11])[CH3:10])=[CH:6][CH:7]=2)=[CH:17][CH:16]=1

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 742994-Chlorophenylboronic acidHCID 2735223N-(4-bromo-2-ethylphenyl)acetamide

Produkt 1

HCID 59450487N-(4'-chloro-3-ethylbiphen-4-yl)acetamideAusbeute 91,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a degassed solution of N-(4-bromo-2-ethylphenyl)acetamide (20 g, 0.082 mol) in toluene (1200 ml) and ethanol (400 ml), 4-chlorobenzene boronic acid (15.5 g, 0.099 mol) is added under an atmosphere of nitrogen, and the reaction mixture is heated to 80° C. Tetrakis(triphenylphosphine)palladium(0) (2.0 g, 0.0017 mol) is added followed by 2M aqueous potassium carbonate solution (160 ml). The reaction mixture is heated at reflux for 4 hours then cooled to room temperature. The reaction mixture is filtered through diatomaceous earth, and the filtrate is evaporated under reduced pressure. The residue is partitioned between ethyl acetate and water. The aqueous phase is extracted with ethyl acetate (3×500 ml) and the organic solutions are combined and concentrated under reduced pressure to give N-(4′-chloro-3-ethylbiphen-4-yl)acetamide (20.5 g).

Aufarbeitung

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 4 hours
  3. temperaturethen cooled to room temperature
  4. filtrationThe reaction mixture is filtered through diatomaceous earth
  5. customthe filtrate is evaporated under reduced pressure
  6. customThe residue is partitioned between ethyl acetate and water
  7. extractionThe aqueous phase is extracted with ethyl acetate (3×500 ml)
  8. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a0c1abc68792466d9fe31d229cb7b1a5
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08828908B2

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