Acetic Acid → 2-Bromomethyl-decafluoropentan-2-ol

Temperature

-20 °C

Heptafluoropropyl iodide (5 g, 16.9 mmole) was stirred in dry diethyl ether (20 ml) at -78° C. Phenylmagnesium bromide (10 ml of a 1.88M solution in ether) was then added dropwise, keeping the temperature below -65° C. When the addition was complete, the reaction mixture was stirred at -20° C. for one hour. It was then cooled to -78° C. and 3-bromo-1,1,1-trifluoropropanone (4.87 g, 18.0 mmole) in dry diethylether (20 ml) was added dropwise, keeping the temperature below -65° C. When the addition was complete, the mixture was stirred at between -20° and -50° C. for four hours. Glacial acetic acid (3 ml) in diethyl ether (5 ml) was then added slowly, followed by water (15 ml). The mixture was then allowed to warm to 5° C. and the phases were separated. The aqueous phase was washed with ether (2×25 ml). The ethereal extracts were combined, dried (MgSO4) and evaporated to give crude 2-bromomethyl-decafluoropentan-2-ol (5.0 g).

1. customthe temperature below -65° C
2. additionWhen the addition
3. temperatureIt was then cooled to -78° C.
4. customthe temperature below -65° C
5. additionWhen the addition
6. stirringthe mixture was stirred at between -20° and -50° C. for four hours
7. temperatureto warm to 5° C.
8. customthe phases were separated
9. washThe aqueous phase was washed with ether (2×25 ml)
10. dry with materialdried (MgSO4)
11. customevaporated

ORD record

ord-ee42249280ba4c588ba02f30508324a1

Source dataset

uspto-grants-1984_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04483862