Phosphorus tribromide → HCID 53871352, compound

Participants

Reaction Steps

Under an argon atmosphere 4.8 grams (0.019 mole) of 12-chloro-12,12-difluoro-10-dodecen-1-ol (prepared in Example 1) was stirred, and 0.65 ml (0.007 mole) of phosphorus tribromide was added dropwise using a syringe. Upon completion of addition, the reaction mixture was stirred at ambient temperature for 18 hours. After this time the reaction mixture was poured into 100 ml of ice/water with stirring. An additional 300 ml of water was added to the gelatinous mixture, and stirring was continued for 18 hours. The mixture was extracted with pentane, and the extract was washed with aqueous sodium bicarbonate. Additional water was added to help separate the layers. The organic layer was washed with an aqueous solution saturated with sodium chloride and then was dried with sodium sulfate. The mixture was filtered, and the filtrate was concentrated under reduced pressure yielding 4.4 grams of 12-chloro-12,12-difluoro-10-dodecenyl bromide. The nmr spectrum was consistent with the proposed structure.

Provenance & Evidence