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

HRID 851125Notes

Reaction equation

HRID 851125 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-butan-2-one and 2,000 ml of ether at 20° to 30° C., while cooling and stirring. The yellowish solution was subsequently stirred, at 20° C., for a further 1 hour and 500 ml of water were then 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 waterpump vacuum. 472 g (80% theory) of 1-bromo-3,3-dimethyl-4-fluoro-butan-2-one of boiling point 80°-90° C./11 mm Hg were obtained. ##STR24##

Workup

  1. temperaturewhile cooling
  2. stirringThe yellowish solution was subsequently 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 waterpump vacuum

Sources & evidence

ORD record
ord-cd9b21c646cb41da9b3e24b31e7fbd77
Source dataset
uspto-grants-1983_05
Patent number
US04382944

Reaction notes

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