Bromide ion → HCID 67913028, compound

Participants

Reaction Steps

A mixture of 1.6 grams (0.005 mole) of 12-chloro-12,12-difluoro-10-dodecenyl bromide and 0.65 gram (0.005 mole) of 4-chlorophenol was stirred, and 0.75 ml (0.005 mole) of DBU was added dropwise. Upon completion of addition, the reaction mixture was stirred at ambient temperature for 18 hours. Gas chromatographic analysis of the reaction mixture indicated the presence of the bromide starting material. An additional 0.5 ml of DBU was added, and the reaction mixture was stirred for 18 hours more. After this time the reaction mixture was shaken with heptane and water. The heptane layer was washed with several portions of water and then with two portions of an aqueous solution saturated with sodium chloride. The organic layer was dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residual oil. The oil was subjected to column chromatography on silica gel. Elution was accomplished using in succession heptane, 20% ethyl acetate in heptane, and 5% ethanol in heptane. The appropriate fractions were combined and concentrated under reduced pressure yielding 0.56 gram of 12-chloro-12,12-difluoro-10-dodecenyl 4-chlorophenyl ether. The nmr spectrum was consistent with the proposed structure.

Provenance & Evidence