Reacción #7459

Ecuación de reacción

water

4-bromobenzyl alcohol

diisopropylethylamine

chloromethyl methyl ether

→

1-bromo-4-[(methoxymethyloxy)methyl]benzene

Rendimiento 86.7%

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónthe mixture was extracted diethyl ether
2. 2
   LavadoThe organic layer was washed with water
3. 3
   Secadodried over anhydrous magnesium sulfate
4. 4
   Otrothe solvent was removed under reduced pressure
5. 5
   OtroThe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=5/1)

Procedimiento

To a solution of 4-bromobenzyl alcohol (2.8 g) and diisopropylethylamine (2.5 g) in dichloromethane (30 mL) was added chloromethyl methyl ether (1.3 g) at 0° C., and the mixture was stirred at room temperature for 14 hours. To the reaction mixture was water, and the mixture was extracted diethyl ether. The organic layer was washed with water and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=5/1) to give 1-bromo-4-[(methoxymethyloxy)methyl]benzene (3.0 g).

Fuente