Ethyl bromoacetate → Ethyl 2-(3,4-dinitrophenoxy)acetate

Reaktionsgleichung

[N+:1]([C:4]1[CH:5]=[C:6]([OH:13])[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])([O-:3])=[O:2].Br[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[N+:1]([C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[O:13][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])([O-:3])=[O:2]

Komponenten

Versuchsvorschrift

A round-bottom flask was charged with 3,4-dinitrophenol (11.04 g, 60 mmol, commercially available from Fluka-Sigma-Aldrich), ethyl bromoacetate (11.02 g, 66 mmol), acetonitrile (120 mL) and cesium carbonate (21.6 g). The mixture was stirred at room temperature overnight. The mixture was filtered, and the recovered solid was washed with ethyl acetate. The filtrate was further diluted with ethyl acetate and water. The aqueous layer was extracted with ethyl acetate and combined organic solvent was washed with saturated brine, dried and concentrated under reduced pressure. The residue was triturated with ether to give ethyl 2-(3,4-dinitrophenoxy)acetate (13.0 g, 80% yield). 1H-NMR (400 MHz, MeOH-d4): δ 8.15 (d, 1H), 7.55 (s, 1H), 7.35 (d, 1H), 4.95 (s, 2H), 4.23 (q, 2H), 1.25 (t, 3H). MS (EI): 271 (MH+).