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

Participants

Reaction Steps

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.

Provenance & Evidence