Acetic Acid → Methyl 2-(4-amino-3-bromophenyl)acetate

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Reaktionsgleichung

[Br:1][C:2]1[CH:3]=[C:4]([CH2:11][C:12]([O:14][CH3:15])=[O:13])[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O.C(O[Na])(C)=O.O.O.O.CC(O)=O>CO.O>[NH2:8][C:7]1[CH:6]=[CH:5][C:4]([CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:3][C:2]=1[Br:1]

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

A mixture of methyl 3-bromo-4-nitrophenylacetate (14.8 g, 53.8 mmol), reduced iron powder (9.62 g, 172 mmol), AcONa.3H2O (7.32 g, 53.8 mmol) and AcOH (20.0 ml) in MeOH/H2O (150/600 ml) was heated at 90° C. for 1 h. After cooled to room temperature, the reaction mixture was filtered through Celite and the filtered cake was washed with MeOH. The combined filtrate were evaporated and extracted with EtOAc. The extracts were washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was chromatographed on silica gel [400 g, CHCl3/EtOAc (20/1)] to give methyl 4-amino-3-bromophenylacetate (9.01 g, 69%) as a brown oil. 1H-NMR (CDCl3) δ3.48 (s, 2H), 3.68 (s, 3H), 4.05 (br, 2H), 6.69 (d, J=8.3 Hz, 1H), 7.00 (dd, J=8.1, 2.0 Hz, 1H), 7.32 (d, J=2.0 Hz, 1H).

Aufarbeitung

temperatureAfter cooled to room temperature
filtrationthe reaction mixture was filtered through Celite
washthe filtered cake was washed with MeOH
customThe combined filtrate were evaporated
extractionextracted with EtOAc
washThe extracts were washed with brine
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customThe residue was chromatographed on silica gel [400 g, CHCl3/EtOAc (20/1)]

Quellen und Nachweise

ORD-Eintrag: ord-1712688776934f9f87928959a38ba43c
Quelldatensatz: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06756378B2

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