1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 54114301, compound

The stirred intermediate 10-bromo-12-chloro-12,12-difluorododecanol, 31.9 grams (0.095 mole), was cooled, and 15.9 grams (0.11 mole) of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) was added dropwise. Upon completion of addition the reaction mixture was allowed to warm to ambient temperature where it was stirred for 16 hours. After this time the reaction mixture was warmed to 70° C. where it was stirred for one hour. The reaction mixture was cooled, and then it was taken up in 200 mL of methylene chloride. The solution was washed in turn with one 150 mL portion of aqueous 1N hydrochloric acid, one 100 mL portion of water, one 100 mL portion of an aqueous solution saturated with sodium bicarbonate, one 100 mL portion of water, and one 100 mL portion 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 distilled under high vacuum yielding 14.3 grams of 12-chloro-12,12-difluoro-10-dodecenol, b.p. 130°-131° C./1.1-1.2 mm.

1. additionUpon completion of addition the reaction mixture
2. temperatureAfter this time the reaction mixture was warmed to 70° C. where it
3. stirringwas stirred for one hour
4. temperatureThe reaction mixture was cooled
5. washThe solution was washed in turn with one 150 mL portion of aqueous 1N hydrochloric acid, one 100 mL portion of water, one 100 mL portion of an aqueous solution saturated with sodium bicarbonate, one 100 mL portion of water, and one 100 mL portion of an aqueous solution saturated with sodium chloride
6. dry with materialThe organic layer was dried with magnesium sulfate
7. filtrationfiltered
8. concentrationThe filtrate was concentrated under reduced pressure to a residual oil
9. distillationThe oil was distilled under high vacuum

ORD record

ord-1869c11b61c94d00af3e7d06fd39ed88

Source dataset

uspto-grants-1990_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04950666