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US4978769A Expired / Lapsed US ⏱️ 0.0 years remaining

Process for introducing fluorine atoms into aromatic rings by nucleophilic exchange

Assignee: Bayer AG
•
Filing: 1989-08-07
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Granted: 1990-12-18
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Expires: 2009-08-07
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Abstract

Abstract Aromatic, ring-fluorinated compounds are particularly advantageously prepared by nucleophilic exchange in the course of reaction wih potassium fluoride in the presence of phase transfer catalysts and, if desired, solvents by carrying out the reaction in the additional presence of metal salts.

Inventors

  • 👤 Ernst Kysela
  • 👤 Rudolf Braden

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-31 23:06
CPC Classifications
C; C07; C07C; C07C253/00; C07C253/30; C07B; C07B39/00; C07C17/00; C07C17/093; C07C17/20; C07C17/202; C07C17/208; C07C201/00; C07C201/06; C07C201/12; C07C51/00; C07C51/347; C07C51/363

Claims Analysis

Total Claims: 7
Claim 1
Independent Claim 150 words
In the preparation of an aromatic ring-fluorinated compound by nucleophilic exchange between an educt and potassium fluoride in the presence of a phase transfer catalyst, the improvement wherein the educt is selected from the group consisting of 3,4-dichloro-nitrobenzene, 2,4-dichloro-nitrobenzene 2,4-dichloro- 5-fluoro-benzoyl chloride, 3,4-dichloro-benzoyl chloride, 2,6-dichloro-benzonitrile, 2-nitro-6-chlorobenzonitrile, 2-trifluoromethyl-4-nitrochlorobenzene, pentachlorobenzotrifluoride, 4-trifluoromethyl-tetrachlorobenzoyl chloride and 3,4,5-trichlorobenzotrifluoride, the phase transfer catalyst is a quaternary nitrogen compound, a quaternary phosphorus compound, a pyridinium salt or a crown ether, and the reaction is effected in the additional presence of a salt of a metal of main groups 3 to 5 of the periodic table of the elements and of sub-group elements, the reaction is effected at from about 100° to 250° C., about 0.1 to 10 moles of the metal salt being present per mole of phase transfer catalyst, and about 0.1 to 20 mole % of the phase transfer catalyst being present based on the educt.
Claim 2
Dependent Claim 150 words
In the preparation of an aromatic ring-fluorinated compound by nucleophilic exchange between an educt and potassium fluoride in the presence of a phase transfer catalyst, the improvement wherein the educt is selected from the group consisting of 3,4-dichloro-nitrobenzene, 2,4-dichloro-nitrobenzene 2,4-dichloro- 5-fluoro-benzoyl chloride, 3,4-dichloro-benzoyl chloride, 2,6-dichloro-benzonitrile, 2-nitro-6-chlorobenzonitrile, 2-trifluoromethyl-4-nitrochlorobenzene, pentachlorobenzotrifluoride, 4-trifluoromethyl-tetrachlorobenzoyl chloride and 3,4,5-trichlorobenzotrifluoride, the phase transfer catalyst is a quaternary nitrogen compound, a quaternary phosphorus compound, a pyridinium salt or a crown ether, and the reaction is effected in the additional presence of a salt of a metal of main groups 3 to 5 of the periodic table of the elements and of sub-group elements, the reaction is effected at from about 100° to 250° C., about 0.1 to 10 moles of the metal salt being present per mole of phase transfer catalyst, and about 0.1 to 20 mole % of the phase transfer catalyst being present based on the educt.
Claim 3
Dependent Claim 26 words
A process according to claim 1, in which dimethyl sulphoxide, N-methylpyrrolidone, tetramethylene sulphone, benzonitrile, nitrobenzene, dimethylacetamide, ethylene glycol demethyl ether or diglyme are employed as solvents.
Claim 4
Dependent Claim 25 words
A process according to claim 1, in which 1.1 to 2 moles of potassium fluoride are employed per mole of fluorine atoms to be introduced.
Claim 5
Dependent Claim 19 words
A process according to claim 1, in which all components of the reaction mixture are employed in dry form.
Claim 6
Dependent Claim 22 words
A process according to claim 1, in which small amounts of water present in the reaction mixture are removed by distilling off.
Claim 7
Dependent Claim 42 words
A process according to claim 1, in which the metal of the salt of a metal of main groups 3 to 5 of the periodic table is selected from the group consisting of chromium, iron, cobalt, nickel, copper, aluminum, zinc and antimony.

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1993-12-17 1994-06-18 1994-12-18 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1997-12-17 1998-06-18 1998-12-18 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2001-12-17 2002-06-18 2002-12-18 $7700.00 Window Closed / Lapsed

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