US4668830A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Process for the preparation of compounds containing a difluoromethylene or trifluoromethyl group
Assignee: Rhone Poulenc Specialites Chimiques
•
Filing: 1985-12-17
•
Granted: 1987-05-26
•
Expires: 2005-12-17
Abstract
Abstract A process for the preparation of compounds containing a difluoromethylene or trifluoromethyl group. A compound containing a carbonyl group, preferbly an acid, acid halide, amide, ketone or any compound containing a perhaloalkylcarbonyl moiety is placed, in anhydrous liquid hydrofluoric acid, in contact with boron trifluoride in a quantity such that the absolute pressure of boron trifluoride in the reaction system is at least one bar for a time sufficient to convert the carbonyl group to a difluormethylene or trifluoromethyl group. The compounds obtained are useful as synthesis intermediates in the pharmaceutical, plant-protection and dye industries, as anesthetics or as heat-transfer and lubricating fluids.
Inventors
- 👤 Michel Desbois
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 20:56
CPC Classifications
C; C07; C07C; C07C41/00; C07C41/01; C07C41/18; C07C41/22; C07B; C07B39/00; C07C17/00; C07C17/093; C07C17/18; C07C37/00; C07C37/01; C07C37/055; C07C37/0555; C07C41/48; C07C41/50
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
92 words
A process for the preparation of a compound containing a difluoromethylene or a trifluoromethyl group comprising the step of contacting a carbonyl-containing compound selected from (a) the group consisting of acids, acid halides, amides and ketones or (b) the group consisting of compounds containing a trihaloalkylcarbonyl group, in anhydrous hydrofluoric acid, with boron trifluoride in a quantity such that the absolute pressure of boron trifluoride in the reaction system is at least one bar for a time sufficient to convert the carbonyl group of said compound to a difluoromethylene or trifluoromethyl group.
Claim 2
Dependent Claim
92 words
A process for the preparation of a compound containing a difluoromethylene or a trifluoromethyl group comprising the step of contacting a carbonyl-containing compound selected from (a) the group consisting of acids, acid halides, amides and ketones or (b) the group consisting of compounds containing a trihaloalkylcarbonyl group, in anhydrous hydrofluoric acid, with boron trifluoride in a quantity such that the absolute pressure of boron trifluoride in the reaction system is at least one bar for a time sufficient to convert the carbonyl group of said compound to a difluoromethylene or trifluoromethyl group.
Claim 3
Dependent Claim
106 words
The process of claim 1, wherein said carbonyl-containing compound has the formula RCOX, wherein R is a moiety selected from the group (1) consisting of (a) linear or branched alkyl, (b) linear or branched haloalkyl and (c) phenyl or the group (2) consisting of perhaloalkyl, wherein when R is selected from the group (1) compounds, X is selected from the group consisting of hydroxy, halo, amino, alkyl, haloalkyl and phenyl moieties, and wherein when R is selected from the group (2) compounds, X is selected from the group consisting of hydroxy, halo, amino, alkyl, haloalkyl, phenyl, alkoxy, haloalkoxy, phenoxy, halophenoxy, alkylthio, haloalkylthio, phenylthio and halophenylthio moieties.
Claim 4
Dependent Claim
30 words
The process of claim 2, wherein said R phenyl moiety is substituted by a moiety selected from the group consisting of alkyl, halo, alkoxy, haloalkyl, phenyl, phenoxy, nitro and amino.
Claim 5
Dependent Claim
30 words
The process of claim 2, wherein said X phenyl moiety is substituted by a moiety selected from the group consisting of alkyl, halo, alkoxy, haloalkyl, phenyl, phenoxy, nitro and amino.
Claim 6
Dependent Claim
20 words
The process of claim 2, wherein said compound RCOX is an acid halide or an ester of a perfluorinated acid.
Claim 7
Dependent Claim
18 words
The process of claim 5, wherein said ester of a perfluorinated acid is an ester of trifluoroacetic acid.
Claim 8
Dependent Claim
33 words
The process of claim 2, wherein said compound RCOX is selected from the group consisting of 4-fluorobenzoyl chloride, isobutyryl chloride, 7-chlorophenyl trifluoroacetate, 4-fluorobenzoic acid, 4-chlorophenyl trifluoroacetate(ester), acetophenone, benzophenone, 4-fluorophenyl trifluoroacetate and 3-trifluoromethylphenyl trifluoroacetate.
Claim 9
Dependent Claim
22 words
The process of claim 1, wherein the molar ratio of hydrofluoric acid to said carbonyl-containing compound is from about 5 to 50.
Claim 10
Dependent Claim
15 words
The process of claim 8, wherein said molar ratio is from about 10 to 30.
Claim 11
Dependent Claim
15 words
The process of claim 8, wherein said molar ratio is from about 10 to 50.
Claim 12
Dependent Claim
19 words
The process of claim 1, wherein the absolute pressure of boron trifluoride is from about 5 to 50 bars.
Claim 13
Dependent Claim
16 words
The process of claim 1, wherein the reaction temperature ranges from about 0° to 150° C.
Claim 14
Dependent Claim
15 words
The process of claim 12, wherein said temperature ranges from about 20° to 80° C.
Claim 15
Dependent Claim
24 words
The process of claim 1, wherein a solvent for said carbonyl-containing compound and/or said compound containing a difluoromethylene or a trifluoromethyl group is included.
Claim 16
Dependent Claim
26 words
The process of claim 14, wherein the solvent is selected from the group consisting of CCl 4 , CHCl 3 and CFCl 2 -CF2C 1 .
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1990-05-25 | 1990-11-24 | 1991-05-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-05-25 | 1994-11-24 | 1995-05-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-05-25 | 1998-11-24 | 1999-05-26 | $7700.00 | Window Closed / Lapsed |