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

Participants

Reaction Steps

A stirred solution of 3.5 grams (0.010 mole) of 3-[4-(3,3-dichloroprop-2-enyloxy)-2,6-dichlorophenoxy]propan-1-ol and 3.3 grams (0.010 mole) of carbon tetrabromide in 50 mL of methylene chloride was cooled to 0–4° C. and 2.9 grams (0.011 mole) of triphenylphosphine was added portion-wise. Upon completion of addition the reaction mixture was allowed to warm to ambient temperature where it stirred during a 42 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 1:3 methylene chloride:hexane as an eluant. The appropriate fractions were combined and concentrated under reduced pressure, yielding 7.7 grams of the subject compound. The NMR spectrum was consistent with the proposed structure.

Provenance & Evidence