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

HRID 1447430
Notes
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Reaction equation

HRID 1447430 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 and 2,000 ml of ether at 20° C. to 30° C., while cooling and stirring. The yellowish solution was subsequently stirred for a further 1 hour at 20° C. and 500 ml of water were then carefully added. 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% of theory) of 1-bromo-3,3-dimethyl-4-fluoro-2-butanone of boiling point 80°-90° C./11 mm Hg were obtained. ##STR29##

Workup

  1. temperaturewhile cooling
  2. stirringThe yellowish solution was subsequently stirred for a further 1 hour at 20° C.
  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-e79b5873639947e59034f55d6f974859
Source dataset
uspto-grants-1982_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04316910

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes