2-Chloro-6-methylaniline → N-(2'-chloro-6'-methylphenyl)-4-methylaniline

HRID 603337

Reaktionsgleichung

Reaktionsgleichung von HRID 603337
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH2:4].Br[C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH:4][C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=1

Komponenten

5

Edukt 3

HCID 68972-Chloro-6-methylanilineHCID 78054-BromotolueneHCID 23676156Sodium t-butoxide

Produkt 1

HCID 57952145N-(2'-chloro-6'-methylphenyl)-4-methylanilineAusbeute 89,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

1.02 g (7.2 mmol) of 2-chloro-6-methylaniline, 1.23 g (7.2 mmol) 4-bromotoluene, 1.15 g (12 mmol) sodium tert-butoxide, 160 mg (0.7 mmol) tri-tert-butyhphosphine and 130 mg (0.23 mmol) bis-dibenzylideneacetone-palladium(0) are reacted in 50 ml toluene under nitrogen at 90° C. for 20 minutes and at 60° C. over night. Aqueous workup (3N HCl, with hyflo, washing the organic phase with water) and flash-chromatography on silica using heptan/toluene (4:1) as the eluent affords 1.49 g of N-(2′-chloro-6′-methylphenyl)-4-methylaniline.

Aufarbeitung

  1. washAqueous workup (3N HCl, with hyflo, washing the organic phase with water) and flash-chromatography on silica

Quellen und Nachweise

ORD-Eintrag
ord-3ceb3f1fa4cf4f2f8c4e63ebb615eccd
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07906677B2

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