Hexafluoroacetone → HCID 10040634, compound

HRID 1655644Notes

Reaction equation

HRID 1655644 reaction equation
[CH2:1]([CH:3]1[O:5][CH2:4]1)[Br:2].[F:6][C:7]([F:15])([F:14])[C:8]([C:10]([F:13])([F:12])[F:11])=[O:9]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[F:6][C:7]([F:15])([F:14])[C:8]1([C:10]([F:13])([F:12])[F:11])[O:5][CH:3]([CH2:1][Br:2])[CH2:4][O:9]1

Participants

5

Reactant 2

HCID 12695HexafluoroacetoneHCID 18430Epibromohydrin

Product 1

HCID 10040634HCID 10040634, compound

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Procedure

This compound was prepared from epibromohydrin and hexafluoroacetone (HFA) (1:1 mole ratio) in the presence of catalytic amounts of tetrabutylammonium bromide and water at 125° C. in 95% isolated yield. Compound 7 has a boiling point 56° C./2 mm. 1H NMR (neat): δ 4.88 (m, 1H), 4.73 (t, J=7.5 Hz, 1H), 4.22 (t, J=7.5 Hz, 1H), 3.60 (m, 2H); 19F NMR (neat: -80.5 (q, J=8.5 Hz, 3F), -81.0 (q, J=8.5 Hz, 3F). Anal. Calc. for C6H5BrF6O2 : C: 23.78, H: 1.66, Br: 26.37, F: 37.62; Found; C: 23.91, H: 1.64, Br: 26.87, F: 37.84.

Workup

  1. customisolated
  2. customyield

Sources & evidence

ORD record
ord-86d9770bd8b04fdf8cc9d20c18c10a4d
Source dataset
uspto-grants-1993_10
Patent number
US05250709

Reaction notes

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