Ethylene Glycol → N-benzyl-4-chloroaniline

HRID 2179178

Reaktionsgleichung

Reaktionsgleichung von HRID 2179178
[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH2:9]([NH2:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[Cl:17][C:18]1[CH:23]=[CH:22][C:21](I)=[CH:20][CH:19]=1.C(O)CO>[Cu]I.CCCCCC.C(OCC)(=O)C.CC(O)C>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([NH:16][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:20][CH:19]=1

Komponenten

8

Edukt 4

HCID 174Ethylene GlycolHCID 7504BenzylamineHCID 125101-Chloro-4-iodobenzeneHCID 62657Potassium Phosphate, Tribasic

Produkt 1

HCID 76281N-benzyl-4-chloroanilineAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 3776IsopropanolLösungsmittelHCID 21226206Ethyl acetate hexaneLösungsmittel

Versuchsvorschrift

The general procedure under argon was followed using copper(I) iodide (10 mg, 0.05 mmol), K3PO4 (425 mg, 2.00 mmol), benzylamine (131 μL, 1.20 mmol), 4-chloroiodobenzene (239 mg, 1.00 mmol), ethylene glycol (111 μL, 2.00 mmol) and 2-propanol (1.0 mL). Column chromatography using a solvent mixture (hexane/ethyl acetate=10/1, Rf=0.4) afforded N-(4-chlorophenyl)benzylamine (182 mg, 84% isolated yield) as light yellow liquid. The spectral data (1H NMR) matched with the literature references and GC analysis indicated >95% purity. See Burton, R. D.; Bartberger, M. D.; Zhang, Y.; Eyler, J. R.; Schanze, K. S. J. Am. Chem. Soc. 1996, 118, 5655-5664.

Quellen und Nachweise

ORD-Eintrag
ord-c09efdd143dd49399821d0e6bfe13515
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09067955B2

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