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

Participants

Reaction Steps

To a solution of 48.40 g of 5-(2-methoxyethoxy)methoxy-1-pentanol (prepared as described in Preparation 39) and 100.19 g of carbon tetrabromide dissolved in 500 ml of methylene chloride was added 79.32 g of triphenylphosphine, whilst ice-cooling (at 5° to 8° C.). The mixture was stirred at room temperature for one hour, after which the solvent was removed by evaporation under reduced pressure. Diethyl ether was then added. 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 from the fractions eluted with a 1:9 by volume mixture of ethyl acetate and hexane, as a colorless oil.

Provenance & Evidence