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

HRID 43321

Reaktionsgleichung

[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>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:12]2[CH:13]=[CH:14][C:15]([CH3:19])=[C:16]([CH:18]=2)[NH2:17])=[CH:4][CH:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 20 °C

Versuchsvorschrift

4-Chlorophenylboronic acid (20.2 g, 0.13 mol) and tetrakis(triphenylphosphine)palladium (0) (3.7 g, 0.003 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 refluxed 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 5-(4-chlorophenyl)-2-methylaniline (21.0 g).

Aufarbeitung

temperaturethe resulting mixture is refluxed for 24 hours
temperatureThe reaction mixture is cooled to room temperature
extractionextracted
dry with materialThe combined organic extracts are dried over anhydrous sodium sulfate
filtrationfiltered
customthe filtrate evaporated in vacuo
customThe residue is further purified by column chromatography on silica gel
washeluting with 7% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag: ord-f4b81713cd4549058b9d8b846e5013ee
Quelldatensatz: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08536351B2

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