Iodine → 3-Fluoro-2-iodoanisole
Reaktionsgleichung
C([Li])CCC.[F:6][C:7]1[CH:8]=[C:9]([O:13][CH3:14])[CH:10]=[CH:11][CH:12]=1.[I:15]I.S([O-])([O-])(=O)=S.[Na+].[Na+]>C1COCC1.CCOCC.O>[F:6][C:7]1[C:8]([I:15])=[C:9]([O:13][CH3:14])[CH:10]=[CH:11][CH:12]=1Komponenten
Reaktionsbedingungen
- Temperatur
- -78 °C
Versuchsvorschrift
n-Butyllithium (1.6 M in hexanes, 26 mL, 42 mmol) was added dropwise to a stirred, cooled (-78° C.) solution of 3-fluoroanisole (5.0 g, 40 mmol) in THF (150 mL) and the mixture was stirred at -78° C. for 2.5 h. Iodine (11.1 g, 43 mmol) in THF (50 mL) was added dropwise and the mixture was allowed to warm to room temperature. Water (200 mL), saturated aqueous sodium thiosulfate (100 mL) and ether (300 mL) were added and the layers were separated. The aqueous layer was extracted with ether (200 mL), the combined organic fractions were dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with hexane/EtOAc (99:1) to give the title compound as a pale yellow oil (7.65 g, 77%). 1H NMR (360 MHz, CDCl3) δ 7.27 (1H, dt, Jd 6.6 Hz, Jt 8.2 Hz), 6.71 (1H, t, J 8.2 Hz), 6.62 (1H, d, J 8.2 Hz), and 3.90 (3H, s).
Aufarbeitung
- temperatureto warm to room temperature
- customthe layers were separated
- extractionThe aqueous layer was extracted with ether (200 mL)
- dry with materialthe combined organic fractions were dried (MgSO4)
- customthe solvent was evaporated under reduced pressure
- customThe residue was purified by column chromatography on silica gel
- washeluting with hexane/EtOAc (99:1)
Quellen und Nachweise
- ORD-Eintrag
- ord-f2936a6600914951983351144ed4c9bc
- Quelldatensatz
- uspto-grants-2000_06
- Patentnummer
- US06071927
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