Reaktion #326815

Reaktionsgleichung

methyl magnesium iodide

magnesium

methyl iodide

4-bromo-2-fluorobenzaldehyde

→

title compound

1-(4-bromo-2-fluorophenyl)ethanol

Lösungsmittel

diethyl ether

diethyl ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   Temperaturthe reaction mixture was cooled to 0° C.
3. 3
   Sonstigequenched with dilute HCl
4. 4
   Extraktionextracted with ethyl acetate
5. 5
   TrocknenThe organic layer was dried over sodium sulphate
6. 6
   Einengenconcentrated under reduced pressure

Vorschrift

To a ice-cold solution of methyl magnesium iodide prepared from magnesium (1.7 g, 73.88 mmoles) and methyl iodide (4.58 ml, 73.88 mmoles) in diethyl ether (50 ml), 4-bromo-2-fluorobenzaldehyde(5 g, 24.62 mmoles) in diethyl ether(10 ml) was added and warmed to room temperature. After 12 h, the reaction mixture was cooled to 0° C., quenched with dilute HCl and extracted with ethyl acetate. The organic layer was dried over sodium sulphate and concentrated under reduced pressure to afford the title compound as red colour liquid (5 g, 94% yield). 1H-NMR (δ ppm, CDCl3, 400 MHz): δ 7.40(t, J=8.2 Hz, 1H), 7.30(dd, J=8.3,1.7 Hz, 1H), 7.21(dd, J=9.9,1.9 Hz, 1H), 5.17(q, J=6.4 Hz, 1H), 1.49(d, J=6.5 Hz, 3H).

Quelle