Water → 1-Bromo-1-(4-chlorophenoxy)-3,3-dimethyl-4-fluoro-2-butanone

HRID 2286766Notes

Reaction equation

HRID 2286766 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][CH2:7][C:8](=[O:14])[C:9]([CH3:13])([CH3:12])[CH2:10][F:11])=[CH:4][CH:3]=1.[Br:17]Br.O>C(Cl)Cl>[Br:17][CH:7]([O:6][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:16][CH:15]=1)[C:8](=[O:14])[C:9]([CH3:12])([CH3:13])[CH2:10][F:11]

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 221632321-(4-Chlorophenoxy)-3,3-dimethyl-4-fluoro-2-butanone

Product 1

HCID 204785111-Bromo-1-(4-chlorophenoxy)-3,3-dimethyl-4-fluoro-2-butanoneYield 78.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

175 g (0.71 mol) of 1-(4-chlorophenoxy)-3,3-dimethyl-4-fluoro-2-butanone were dissolved in 500 ml of methylene chloride, and 114 g (0.71 mol) of bromine were added dropwise at 20° to 30° C., while stirring and cooling. The mixture was subsequently stirred at 20° C. for 2 hours, 200 ml of water were added carefully and the methylene chloride phase was washed several times with ice-water and dried over sodium sulphate. After distilling off the solvent in vacuo, the residue was recrystallized from cyclohexane. 180 g (78% of theory) of 1-bromo-1-(4-chlorophenoxy)-3,3-dimethyl-4-fluoro-2-butanone of melting point 73° to 75° C. were obtained. ##STR16##

Workup

  1. temperaturecooling
  2. stirringThe mixture was subsequently stirred at 20° C. for 2 hours
  3. washthe methylene chloride phase was washed several times with ice-water
  4. dry with materialdried over sodium sulphate
  5. distillationAfter distilling off the solvent in vacuo
  6. customthe residue was recrystallized from cyclohexane

Sources & evidence

ORD record
ord-46a4a842a3234b7c9b7e8f58639c8fc9
Source dataset
uspto-grants-1981_05
Patent number
US04267381

Reaction notes

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