Réaction #486419

Équation de réaction

NaH

1-bromo-2-hydroxy-4-methoxybenzene

bromomethyl methyl ether

→

title compound

1-Bromo-4-methoxy-2-methoxymethoxybenzene

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwere dropwise added
2. 2
   Autreit was then quenched cautiously by the addition of cold dilute HCl
3. 3
   Extractionextracted with EtOAc
4. 4
   ExtractionThe EtOAc extract
5. 5
   Lavagewas washed successively with
6. 6
   AutreAfter drying
7. 7
   Filtration(MgSO4) filtration and evaporation
8. 8
   Autregave liquid
9. 9
   workup.DISTILLATIONThe product was purified by distillation (85° C., 0.2 mm Hg)

Mode opératoire

To a suspension of NaH (2.5 g, 0.06 mol) in dry DMF (100 mL) at 0° C. was added solution of 1-bromo-2-hydroxy-4-methoxybenzene (10.6 g, 0.05 mol). After stirring at 0° C. for 30 min. bromomethyl methyl ether (7.8 g, 0.06 mmol) were dropwise added. The mixture was warmed to room temperature over 20 min. and then stirred for 2 h, it was then quenched cautiously by the addition of cold dilute HCl and extracted with EtOAc. The EtOAc extract was washed successively with; H2O, 5% aqueous NaHCO3, H2O and finally brine. After drying (MgSO4) filtration and evaporation gave liquid. The product was purified by distillation (85° C., 0.2 mm Hg) to give the title compound as a colorless oil (13.7 g, 97%).

Source