Reaction #2067098

Reaction equation

3-bromo-1,1,1-trifluoropropanone

Phenylmagnesium bromide

Heptafluoropropyl iodide

acetic acid

→

2-bromomethyl-decafluoropentan-2-ol

Yield 82.0%

Solvents

diethylether

ether

diethyl ether

water

diethyl ether

Conditions

Workup

1. 1
   Otherthe temperature below -65° C
2. 2
   workup.ADDITIONWhen the addition
3. 3
   TemperatureIt was then cooled to -78° C.
4. 4
   Otherthe temperature below -65° C
5. 5
   workup.ADDITIONWhen the addition
6. 6
   workup.STIRRINGthe mixture was stirred at between -20° and -50° C. for four hours
7. 7
   Temperatureto warm to 5° C.
8. 8
   Otherthe phases were separated
9. 9
   WashThe aqueous phase was washed with ether (2×25 ml)
10. 10
    Dryingdried (MgSO4)
11. 11
    Otherevaporated

Procedure

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).

Source