Acetic Acid → 2-(Benzyloxy)-4-fluoroaniline
Reaktionsgleichung
C(O)(=O)C.[F:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[C:8]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:7]=1>C(OCC)(=O)C.[Fe]>[F:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[C:8]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:7]=1Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 76 °C
Versuchsvorschrift
To a mixture of iron powder (90.36 g, 1.62 mol) and acetic acid (10%, 400 mL) at 80° C. was added a solution of the title compound of Step A (40 g, 0.162 mol) in ethyl acetate (200 mL) dropwise with vigorous stirring. The reaction mixture was stirred further at 76° C. for 1 h. After the reaction was complete, the hot reaction mixture was filtered through Celite® (200 g) and the filter cake was washed with ethyl acetate (1000 mL). The filtrate was washed with water (3×200 mL), sodium bicarbonate solution (5%, 3×200 mL), dried (MgSO4) and concentrated to give the crude product. The product was purified by flash chromatography to give 24.76 g of the title compound of Step B. 1H NMR (CDCl3, 400 MHz): δ7.41 (m,5H), 6.60 (m,3H), 5.04 (s,2H).
Aufarbeitung
- filtrationthe hot reaction mixture was filtered through Celite® (200 g)
- washthe filter cake was washed with ethyl acetate (1000 mL)
- washThe filtrate was washed with water (3×200 mL), sodium bicarbonate solution (5%, 3×200 mL)
- dry with materialdried (MgSO4)
- concentrationconcentrated
- customto give the crude product
- customThe product was purified by flash chromatography
Quellen und Nachweise
- ORD-Eintrag
- ord-08479fc24d0343a9b5cdf9355c466806
- Quelldatensatz
- uspto-grants-1998_05
- Patentnummer
- US05750471
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