Benzyl Bromide → 12,12-Difluoro-11-dodecenyl phenylmethyl ether

Participants

Reaction Steps

Under a nitrogen atmosphere a stirred mixture of 0.18 gram (0.0075 mole) of sodium hydride in 25 ml of tetrahydrofuran was cooled in an ice-bath, and 1.5 grams (0.0068 mole) of 12,12-difluoro-11-dodecen-1-ol (prepared in Example 5) was added dropwise. Upon completion of addition and when the evolution of hydrogen ceased, a solution of 1.2 grams (0.0068 mole) of phenylmethyl bromide in 5 ml of tetrahydrofuran was added dropwise. Upon completion of addition, the reaction mixture was stirred at ambient temperature for 18 hours. After this time the reaction mixture was taken up in 150 ml of diethyl ether and was washed with 50 ml of water and then with 50 ml of an aqueous solution saturated with sodium chloride. The organic layer was dried with magnesium 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 methylene chloride. The appropriate fractions were combined and concentrated under reduced pressure yielding 0.8 gram of 12,12-difluoro-11-dodecenyl phenylmethyl ether. The nmr spectrum was consistent with the proposed structure.

Provenance & Evidence