Water → 1-Bromo-4-(ethoxymethyl)benzene

In DMF (120 ml) was dissolved 4-bromobenzyl alcohol (10.1 g). To the mixture was added under ice-cooling 65% sodium hydride (3.6 g), and the mixture was stirred at room temperature for 3 hours. To the mixture was added dropwise at room temperature iodoethane (12.6 g),and the mixture was stirred at room temperature for 2 hours. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate, washed with saturated brine and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated, and the residue was purified with silica gel column chromatography (hexane/ethyl acetate=8/1) to give 1-bromo-4-(ethoxymethyl)benzene (10.1 g).

1. additionTo the mixture was added under ice-
2. stirringthe mixture was stirred at room temperature for 2 hours
3. extractionthe mixture was extracted with ethyl acetate
4. washwashed with saturated brine
5. dry with materialdried with magnesium sulfate
6. customUnder reduced pressure, the solvent was evaporated
7. customthe residue was purified with silica gel column chromatography (hexane/ethyl acetate=8/1)

ORD record

ord-46b5ce56421d48cda158d144f3cc7af2

Source dataset

uspto-grants-2001_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06235771B1