2,4-Dichlorophenol → 1-(2,4-Dichlorophenoxy)-3,3-dimethyl-4-fluoro-2-butanone

HRID 1649182Notes

Reaction equation

HRID 1649182 reaction equation
Br[CH2:2][C:3](=[O:9])[C:4]([CH3:8])([CH3:7])[CH2:5][F:6].[Cl:10][C:11]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=1[OH:18].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:10][C:11]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=1[O:18][CH2:2][C:3](=[O:9])[C:4]([CH3:8])([CH3:7])[CH2:5][F:6]

Participants

5

Reactant 3

HCID 84492,4-DichlorophenolHCID 11430Potassium CarbonateHCID 130194421-Bromo-3,3-dimethyl-4-fluoro-2-butanone

Product 1

HCID 130194431-(2,4-Dichlorophenoxy)-3,3-dimethyl-4-fluoro-2-butanoneYield 90.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
20 °C

Procedure

157 g (0.79 mol) of 1-bromo-3,3-dimethyl-4-fluoro-2-butanone were added dropwise to a stirred mixture of 129 g (0.79 mol) of 2,4-dichlorophenol and 110 g (0.79 mol) of powdered potassium carbonate in 500 ml of acetone at 20° to 30° C., while cooling. The mixture was subsequently stirred at 20° C. for 2 hours, the inorganic salt was filtered off and the filtrate was concentrated. 199.3 g (90% of theory) of 1-(2,4-dichlorophenoxy)-3,3-dimethyl-4-fluoro-2-butanone were obtained as an oil, which was further reacted directly. ##STR82##

Workup

  1. temperaturewhile cooling
  2. filtrationthe inorganic salt was filtered off
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-11afaf96c03e4f0384b30d904f53edf1
Source dataset
uspto-grants-1983_11
Patent number
US04415586

Reaction notes

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