Sodium Carbonate → 5-(4-Chlorophenyl)-2-methylaniline

HRID 72245

Reaktionsgleichung

Reaktionsgleichung von HRID 72245
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.Br[C:12]1[CH:13]=[CH:14][C:15]([CH3:19])=[C:16]([CH:18]=1)[NH2:17].C(=O)([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>[NH2:17][C:16]1[CH:18]=[C:12]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH:13]=[CH:14][C:15]=1[CH3:19]

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 27348055-Bromo-o-toluidine

Produkt 1

HCID 233905465-(4-Chlorophenyl)-2-methylanilineAusbeute 96,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

Tetrakis(triphenylphosphine)palladium (0) (3.7 g, 0.003 mol) and 4-chlorophenylboronic acid (20.2 g, 0.13 mol) are added to a solution of 5-bromo-2-methylaniline (20 g, 0.1 mol) in 1,2-dimethoxyethane (200 ml). After stirring the reaction mixture for 15 minutes at 20° C., a solution of 20% aqueous sodium carbonate (300 ml) is added to the mixture, and the resulting mixture is heated at reflux for 24 hours. The reaction mixture is cooled to room temperature, diluted with water (600 ml) and extracted using ethyl acetate. The combined organic extracts are dried over anhydrous sodium sulfate, filtered and the filtrate evaporated in vacuo. The residue is further purified by column chromatography on silica gel, eluting with 7% ethyl acetate in hexane to give 3-amino-4′-chloro-4-methylbiphenyl (21.0 g).

Aufarbeitung

  1. temperaturethe resulting mixture is heated
  2. temperatureat reflux for 24 hours
  3. temperatureThe reaction mixture is cooled to room temperature
  4. extractionextracted
  5. dry with materialThe combined organic extracts are dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customthe filtrate evaporated in vacuo
  8. customThe residue is further purified by column chromatography on silica gel
  9. washeluting with 7% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-e21403b9ac7543eabf75bf5ff62f0a7a
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08828908B2

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