Stannous Chloride → 5-Chloro-2-phenoxyaniline

HRID 883908

Reaktionsgleichung

Reaktionsgleichung von HRID 883908
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:4]([N+:15]([O-])=O)[CH:3]=1.Cl[Sn]Cl>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:4]([NH2:15])[CH:3]=1

Komponenten

3

Edukt 2

HCID 24479Stannous ChlorideHCID 8911814-Chloro-2-nitro-1-phenoxybenzene

Produkt 1

HCID 667385-Chloro-2-phenoxyanilineAusbeute 79 %

Versuchsvorschrift

To a solution of DMF (50 mL) was added 1-bromo-2-nitro-4-chloro-benzene (5.0 g, 21.1 mmol), phenol (1.9 g, 21.1 mmol), and Na2CO3 (2.3 g, 21.1 mmol). The solution was heated to 85° C. and stirred overnight. The reaction was poured into water and extracted with EtOAc. Washed with water and dried over Na2SO4, filtered and concentrated under vacuum giving a yellow oil that was purified by silica gel column chromatography eluting with Hexanes:Ethyl Acetate (90:10) to give 4-chloro-2-nitro-1-phenoxy-benzene (3.8 g, 74%). 4-Chloro-2-nitro-1-phenoxy-benzene (13 g, 52.1 mmol) was reacted with SnCl2 (49.3 g, 260 mmol) following the procedure from Example 7f giving 5-chloro-2-phenoxy-phenylamine as a white solid 9.0 g, 79%).

Quellen und Nachweise

ORD-Eintrag
ord-befd39fa4aa04122ae3cf9fd178056ba
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08236950B2

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