5-Benzyloxy-2-fluoro-4-methylnitrobenzene → 5-Benzyloxy-2-fluoro-4-methylaniline

HRID 7496

Reaktionsgleichung

[CH2:1]([O:8][C:9]1[C:10]([CH3:19])=[CH:11][C:12]([F:18])=[C:13]([N+:15]([O-])=O)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(=O)C.O.[Fe]>[CH2:1]([O:8][C:9]1[C:10]([CH3:19])=[CH:11][C:12]([F:18])=[C:13]([CH:14]=1)[NH2:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

The starting material, 5-benzyloxy-2-fluoro-4-methylaniline, was obtained by adding iron powder (2.88 g, 51 mmol), in portions, to a solution of 5-benzyloxy-2-fluoro-4-methylnitrobenzene (4.8 g, 18 mmol) in acetic acid (33 ml) and water (5.7 ml), at ambient temperature. The mixture was heated and after stirring at 100° C. for 10 minutes, it was cooled and partitioned between ethyl acetate and water. The organic layer was washed with water, aqueous saturated sodium carbonate solution and then brine, dried (MgSO4) and the solvent evaporated. The residue was purified by flash chromatography using petroleum ether/ethyl acetate (8/2) as eluent to give 5-benzyloxy-2-fluoro-4-methylaniline (3.65 g, 87%).

Aufarbeitung

customat ambient temperature
temperatureThe mixture was heated
temperatureit was cooled
custompartitioned between ethyl acetate and water
washThe organic layer was washed with water, aqueous saturated sodium carbonate solution
dry with materialbrine, dried (MgSO4)
customthe solvent evaporated
customThe residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag: ord-c8db631387344b1d934a549994ef9606
Quelldatensatz: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07087602B2

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