US4978769A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Process for introducing fluorine atoms into aromatic rings by nucleophilic exchange
Assignee: Bayer AG
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Filing: 1989-08-07
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Granted: 1990-12-18
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Expires: 2009-08-07
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.
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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 |