Diethyl Ether → 1-Bromo-3,3-dimethyl-4-fluoro-2-butanone

HRID 2286764Notes

Reaction equation

HRID 2286764 reaction equation
[Br:1]Br.[CH3:3][C:4]([CH3:10])([CH2:8][F:9])[C:5](=[O:7])[CH3:6].CCOCC>O>[Br:1][CH2:6][C:5](=[O:7])[C:4]([CH3:10])([CH3:3])[CH2:8][F:9]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 24408BromineHCID 130194414-Fluoro-3,3-dimethylbutan-2-one

Product 1

HCID 130194421-Bromo-3,3-dimethyl-4-fluoro-2-butanoneYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

480 g of bromine were slowly added dropwise to a mixture of 354 g (3 mol) of 3,3-dimethyl-4-fluoro-2-butanone (see Example 1) and 2000 ml of ether at 20° to 30° C., while cooling and stirring. The yellowish solution was then stirred at 20° C. for a further 1 hour, and 500 ml of water were subsequently added carefully. The ether phase was separated off, washed several times with water and dried over sodium sulphate. After distilling off the solvent, the residue was distilled under a water-pump vacuum. 472 g (80% of theory) of 1-bromo-3,3-dimethyl-4-fluoro-2-butanone of boiling point 80° to 90° C./11 mm Hg were obtained. ##STR14##

Workup

  1. temperaturewhile cooling
  2. stirringThe yellowish solution was then stirred at 20° C. for a further 1 hour
  3. customThe ether phase was separated off
  4. washwashed several times with water
  5. dry with materialdried over sodium sulphate
  6. distillationAfter distilling off the solvent
  7. distillationthe residue was distilled under a water-pump vacuum

Sources & evidence

ORD record
ord-617d00c7e2fb4a478c5806da2853dd66
Source dataset
uspto-grants-1981_05
Patent number
US04267381

Reaction notes

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