Reaktion #452537

Reaktionsgleichung

bromomethyl methylether

1-Bromo-2-hydroxy-4-methoxybenzene

sodium hydride

→

title compound

Ausbeute 106.9%

1-Bromo-2-methoxymethoxy-4-methoxybenzene

Ausbeute 106.9%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGAfter stirring for 1 h at 0° C. the reaction
2. 2
   Sonstigewas quenched with water
3. 3
   ExtraktionThe mixture was extracted with ethyl acetate
4. 4
   Waschenthe combined organic extracts were washed with brine
5. 5
   Trocknendried (Na2SO4)
6. 6
   SonstigeRemoval of the solvent

Vorschrift

To a solution of 1-Bromo-2-hydroxy-4-methoxybenzene (5.00 g, 24.60 mmol) in DMF was added 60% sodium hydride (1.97 g, 49.20 mmol) at 0° C. under argon. The mixture was allowed to stir at 0° C. for 15 minutes, then 90% bromomethyl methylether (4.10 g, 29.50 mmol) was added. After stirring for 1 h at 0° C. the reaction was quenched with water. The mixture was extracted with ethyl acetate and the combined organic extracts were washed with brine and dried (Na2SO4). Removal of the solvent afforded the title compound as an oil (6.5 g, quantitative yield). 1H NMR (400 MHz, CDCl3) δ 7.41 (d, 2H), 6.76 (d, 1H), 6.47 (dd, 1H), 5.24 (s, 2H), 3.87 (s, 3H), 3.53 (s, 3H).

Quelle