Carbon tetrabromide → 1-Bromo-5-(2-methoxyethoxy)methoxypentane

79.32 g of triphenylphosphine were added, whilst ice-cooling (at 5° to 8° C.), to a solution of 48.40 g of 5-(2-methoxyethoxy)methoxy-1-pentanol (prepared as described in Preparation 59) and 100.19 g of carbon tetrabromide dissolved in 500 ml of methylene chloride. The mixture was stirred at room temperature for 1 hour, after which the solvent was removed by evaporation under reduced pressure. Diethyl ether was then added to the resulting residue. The insoluble materials were filtered off, and the filtrate was concentrated by evaporation under reduced pressure. The residue was subjected to column chromatography through 850 g of silica gel, and 57.87 g of the title compound were obtained, as a colorless oil, from those fractions eluted with a 1:9 by volume mixture of ethyl acetate and hexane.

1. temperaturecooling (at 5° to 8° C.)
2. customafter which the solvent was removed by evaporation under reduced pressure
3. additionDiethyl ether was then added to the resulting residue
4. filtrationThe insoluble materials were filtered off
5. concentrationthe filtrate was concentrated by evaporation under reduced pressure

ORD record

ord-3ad68c69837842ba93bfda9497e02e36

Source dataset

uspto-grants-1990_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04891363