N,N-Dimethylglycine → Ethyl 2-nitro-4-(3-nitrophenoxy)benzeneacetate

HRID 422034

Reaktionsgleichung

[N+:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[CH2:11]([O:13][C:14](=[O:26])[CH2:15][C:16]1[CH:21]=[CH:20][C:19](Br)=[CH:18][C:17]=1[N+:23]([O-:25])=[O:24])[CH3:12].CN(C)CC(O)=O.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.O.[Cu](I)I>[CH2:11]([O:13][C:14](=[O:26])[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:10][C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)=[CH:18][C:17]=1[N+:23]([O-:25])=[O:24])[CH3:12]

Komponenten

Reaktionsbedingungen

Temperatur: 120 °C

Versuchsvorschrift

To a sealed tube are charged with 3-nitrophenol (83 mg, 0.6 mmol), (4-bromo-2-nitro-phenyl)-acetic acid ethyl ester (180 mg, 0.63 mmol), copper iodide (12 mg, 0.06 mmol), N,N-dimethylglycine (23 mg, 0.2 mmol), Cs2CO3 (400 mg, 1.2 mmol) in 1,4-dioxane. The resulting mixture is stirred at 120° C. for 24 h. The reaction mixture is diluted with water and extracted with EtOAc. The organic phase is dried, concentrated, and purified by flash column chromatography (DCM/Hexane=9:1) to give 130 mg of the desired product (yield 62%). 1H NMR (400 MHz, CDCl3) δ 8.00-7.97 (m, 1 H), 7.82-7.81 (m, 1 H), 7.70-7.69 (m, 1 H), 7.53-7.49 (m, 1 H), 7.34-7.30 (m, 1 H), 7.22-7.19 (m, 1 H), 4.14-4.09 (m, 2 H), 3.94 (s, 2 H), 1.23-1.18 (m, 3 H). LC/MS: 347.2 (MH+).

Aufarbeitung

extractionextracted with EtOAc
customThe organic phase is dried
concentrationconcentrated
custompurified by flash column chromatography (DCM/Hexane=9:1)

Quellen und Nachweise

ORD-Eintrag: ord-13f11246c1dc4bf793ff91d0a7abc312
Quelldatensatz: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08101608B2

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