4-Chlorophenol → 3,3-Bisfluoromethyl-1-(4-chlorophenoxy)-butan-2-one

HRID 1649176Notes

Reaction equation

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

Participants

Conditions

Temperature: 40 °C

Procedure

171.2 g (0.79 mol) of 3,3-bisfluoromethyl-1-bromo-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. The mixture was subsequently stirred at 40° C. for 4 hours, the inorganic salt was filtered off and the filtrate was concentrated. The residue was distilled under a high vacuum. 190.5 g (90% of theory) of 3,3-bisfluoromethyl-1-(4-chlorophenoxy)-butan-2-one of boiling point 113°-117° C./0.1 mm Hg were obtained. ##STR74##

Workup

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

Sources & evidence

ORD record: ord-e52d73ad85174408a2c1e0776f016ee9
Source dataset: uspto-grants-1983_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04415586

Reaction notes

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