Phosphorus tribromide → HCID 53871352, compound

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.

1. additionUpon completion of addition
2. stirringwith stirring
3. stirringstirring
4. waitwas continued for 18 hours
5. extractionThe mixture was extracted with pentane
6. washthe extract was washed with aqueous sodium bicarbonate
7. additionAdditional water was added
8. customto help separate the layers
9. washThe organic layer was washed with an aqueous solution saturated with sodium chloride
10. dry with materialwas dried with sodium sulfate
11. filtrationThe mixture was filtered
12. concentrationthe filtrate was concentrated under reduced pressure

ORD record

ord-028e46959c3c43adbf1396e24569101e

Source dataset

uspto-grants-1992_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05081287