Carbon tetrabromide → 1-[4-(3,3-Dichloroprop-2-enyloxy)-2,6-dichlorophenoxy]-4-bromobutane

Participants

Reaction Steps

A stirred solution of 7.3 grams (0.020 mole) of 4-[4-(3,3-dichloroprop-2-enyloxy)-2,6-dichlorophenoxy]butan-1-ol in 400 mL of methylene chloride was cooled in an ice bath and, in turn, 5.5 grams (0.021 mole) of triphenylphosphine and 6.9 grams (0.021 mole) of carbon tetrabromide were added. Upon completion of addition the reaction mixture was stirred with continued cooling for one hour, then it was allowed to warm to ambient temperature where it stirred during an 18-hour period. After this time the reaction mixture was concentrated under reduced pressure to a residue. The residue was purified with column chromatography on silica gel using hexane and a mixture of 1:1 methylene chloride and heptane as an eluant. The appropriate fractions were combined and concentrated under reduced pressure, yielding 12.2 grams of the subject compound. The NMR spectrum was consistent with the proposed structure.

Provenance & Evidence