Isopropyl iodide → 4-Fluoro-1-nitro-2-(propan-2-yloxy)benzene

Reaktionsgleichung

[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([OH:8])[CH:7]=1.I[CH:13]([CH3:15])[CH3:14].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([O:8][CH:13]([CH3:15])[CH3:14])[CH:7]=1

Komponenten

Versuchsvorschrift

A mixture of 5-fluoro-2-nitrophenol (2.5 g, 15.9 mmol), 2-iodopropane (5.4 g, 31.8 mmol), and potassium carbonate (4.2 g, 39.8 mmol) in acetone (40 mL) was heated to reflux for 16 hours. The mixture was cooled and evaporated under vacuum, and the residue was partitioned between ethyl acetate (100 mL) and water (150 mL), and the aqueous phase was extracted with ethyl acetate (100 mL). The combined organic layers were washed with water (3×150 mL), dried (MgSO4), and evaporated, providing 3.2 g, in quantitative yield; 1H NMR (CDCl3) δ 1.42 (d, J=6.0 Hz, 6H), 4.63 (septet, J=6.0 Hz, 6H), 6.64-6.72 (m, 1H), 6.76 (dd, J=9.8 Hz, J=2.5 Hz, 1H), 7.88 (dd, J=8.9 Hz, J=6.1 Hz, 1H).