2-(2,4-Dichlorophenoxy)ethanol → 1-(2-Bromoethoxy)-2,4-dichlorobenzene

To a solution of 10.0 g of 2-(2,4-dichlorophenoxy)-1-ethanol in 1,2-dimethoxyethane (200 ml) was added dropwise a solution of 14 g of phosphorus tribromide in 1,2-dimethoxyethane (20 ml) under ice-cooling. The reaction solution was stirred at room temperature for 20 hours. After the reaction solution was concentrated, the residue was diluted with water and ethyl acetate. Saturated aqueous sodium hydrogencarbonate was added to the organic layer, and the resulting emulsion formed was subjected to Celite filtration. The filtrate was diluted with diethyl ether and saturated aqueous ammonium chloride. The organic layer was dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography, to give 6.15 g of the title compound as a pale yellow oil.

1. temperaturecooling
2. concentrationAfter the reaction solution was concentrated
3. additionthe residue was diluted with water and ethyl acetate
4. additionSaturated aqueous sodium hydrogencarbonate was added to the organic layer
5. customthe resulting emulsion formed
6. filtrationwas subjected to Celite filtration
7. additionThe filtrate was diluted with diethyl ether and saturated aqueous ammonium chloride
8. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
9. concentrationconcentrated
10. customThe residue was purified by silica gel column chromatography

ORD record

ord-0ec5eb26f10940d681783126eddadd31

Source dataset

uspto-grants-2009_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07544835B2