Hydrogen Peroxide → 1,3-Difluoro-2-methoxy-4-nitrobenzene
Reaktionsgleichung
FC(F)(F)C(OC(=O)C(F)(F)F)=[O:4].OO.[F:16][C:17]1[C:22]([O:23][CH3:24])=[C:21]([F:25])[CH:20]=[CH:19][C:18]=1[NH2:26].[Cl-].[Na+].[OH2:29]>C(Cl)Cl>[F:25][C:21]1[CH:20]=[CH:19][C:18]([N+:26]([O-:4])=[O:29])=[C:17]([F:16])[C:22]=1[O:23][CH3:24]Komponenten
Versuchsvorschrift
To a solution of trifluoroacetic anhydride (26.2 mL, 0.19 mol) in DCM (100 mL) at 0° C. was added, dropwise, hydrogen peroxide (50% in water, 12.9 mL, 0.17 mol) and the reaction mixture was stirred at 0° C. for 1.5 h. 2,4-Difluoro-3-methoxyphenylamine (3 g, 18.9 mmol) was added as a solution in DCM (20 mL) and the reaction mixture stirred at RT for 3 h. The reaction mixture was diluted with brine and extracted with DCM (3×30 mL). The combined organic fractions were washed with sat. aq. NaHCO3 solution, dried (MgSO4) and concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2, eluting with 0-100% Et2O in cyclohexane) to give the title compound as a colourless solid (2.03 g, 57%). 1H NMR 400 MHz δ (CDCl3): 7.83-7.76 (1H, m), 7.03 (1H, td, J=9.4, 2.5 Hz), 4.08 (3H, t, J=1.1 Hz).
Aufarbeitung
- extractionextracted with DCM (3×30 mL)
- washThe combined organic fractions were washed with sat. aq. NaHCO3 solution
- dry with materialdried (MgSO4)
- concentrationconcentrated in vacuo
- washThe resultant residue was subjected to flash chromatography (SiO2, eluting with 0-100% Et2O in cyclohexane)
Quellen und Nachweise
- ORD-Eintrag
- ord-c99f3b63bec646a9971dad90cb26ee8c
- Quelldatensatz
- uspto-grants-2014_02
- Patentnummer
- US08653089B2
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