Bromine → 1-Bromo-3,3,4,4,4-pentafluorobutan-2-one

HRID 2290299Notes

Reaction equation

HRID 2290299 reaction equation
[F:1][C:2]([C:8]([CH3:10])=[O:9])([F:7])[C:3]([F:6])([F:5])[F:4].[Br:11]Br>S(=O)(=O)(O)O>[Br:11][CH2:10][C:8](=[O:9])[C:2]([F:7])([F:1])[C:3]([F:6])([F:5])[F:4]

Participants

4

Procedure

Methyl pentafluoroethyl ketone (3.9 g, 0.02407 mole) (JACS, 78, 2268-70 [1956]) was stirred in concentrated sulphuric acid (10 ml) at room temperature under a dry-ice condenser. Bromine (1.92 g; 0.012035 mole) was added slowly over two hours with vigorous stirring. The mixture was then stirred for one hour at room temperature and then at 50° C. for one hour. The resulting amber solution was distilled at atmospheric pressure, yielding one main fraction of 4.41 g (76%), boiling at 94-97° C. The mass spectrum confirmed the structure, showing parent ions at 240 and 242 m/e corresponding to C4H2BrF5O (2 isotopes of Br).

Workup

  1. waitat 50° C. for one hour
  2. distillationThe resulting amber solution was distilled at atmospheric pressure
  3. customyielding one main fraction of 4.41 g (76%), boiling at 94-97° C

Sources & evidence

ORD record
ord-1c10e4ccfd1c4a0da41bce1baf744631
Source dataset
uspto-grants-1986_10
Patent number
US04616027

Reaction notes

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