4-Chlorophenol → 1-(4-Chlorophenoxy)-3,3-dimethyl-4-fluoro-2-butanone

HRID 851126Notes

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

Participants

Conditions

Temperature: 20 °C

Procedure

157 g (0.79 mol) of 1-bromo-3,3-dimethyl-4-fluoro-butan-2-one were added dropwise to a stirred mixture of 102 g (0.79 mol) of p-chlorophenol and 110 g (0.79 mol) of powdered potassium carbonate in 500 ml of acetone at 20° to 30° C., whilst cooling. The mixture was subsequently stirred at 20° C. for 2 hours, the inorganic salt was filtered off and the filtrate was concentrated. The residue was distilled under a high vacuum. 175 g (90% of theory) of 1-(4-chlorophenoxy)-3,3-dimethyl-4-fluoro-butan-2-one of boiling point 112°-119° C./0.05 mm Hg were obtained. ##STR25##

Workup

temperaturewhilst cooling
filtrationthe inorganic salt was filtered off
concentrationthe filtrate was concentrated
distillationThe residue was distilled under a high vacuum

Sources & evidence

ORD record: ord-35f5b209a34a4e9faaef65f7fa435db1
Source dataset: uspto-grants-1983_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04382944

Reaction notes

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