4-Bromo-2-methylaniline → 4'-Chloro-3-methylbiphen-4-ylamine

HRID 341679Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 341679
Br[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([CH3:9])[CH:3]=1.[Cl:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=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:10][C:11]1[CH:16]=[CH:15][C:14]([C:2]2[CH:3]=[C:4]([CH3:9])[C:5]([NH2:6])=[CH:7][CH:8]=2)=[CH:13][CH:12]=1

Komponenten

7

Edukt 3

HCID 114234-Bromo-2-methylanilineHCID 11430Potassium CarbonateHCID 742994-Chlorophenylboronic acid

Produkt 1

HCID 230051884'-Chloro-3-methylbiphen-4-ylamineAusbeute 70,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a stirred, degassed solution of 4-bromo-2-methylaniline (20 g, 0.107 mol) in toluene (1200 ml) and ethanol (400 ml), under an atmosphere of nitrogen, is added 4-chlorophenylboronic acid (20.32 g, 0.13 mol) and the reaction mixture is stirred and heated to 80° C. Tetrakis(triphenylphosphine)palladium(0) (2.48 g, 0.002 mol) is added to the reaction mixture, and to this is added 2M aqueous potassium carbonate solution (160 ml). The reaction mixture is refluxed 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 extracts are combined and concentrated under reduced pressure to give 4′-chloro-3-methylbiphen-4-ylamine (16.5 g).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-9448fec464d840f59506ae2b53885044
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895761B2

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