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US4173706A
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Process for producing fluorinated organic compounds containing a difluoromethylene group from compounds comprising at least one carbonyl function
Assignee: Institut de Recherches Chimiques et Biologiques Appliquees SARL IRCEBA
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Filing: 1978-04-06
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Granted: 1979-11-06
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Expires: 1998-04-06
Abstract
Abstract A novel process for producing fluorinated organic compounds containing a difluoromethylene group, essentially characterized by reacting organic compounds containing a carbonyl function with molybdenum hexafluoride at room temperature and under atmospheric pressure.
Inventors
- 👤 Francois Mathey
- 👤 Jean Bensoam
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 21:52
CPC Classifications
C; C07; C07D; C07D209/00; C07D209/02; C07D209/44; C07D209/48; C07B; C07B39/00; C07C; C07C17/00; C07C17/093; C07C17/18; C07C19/00; C07C19/08; C07C201/00; C07C201/06; C07C201/12; C07C209/00; C07C209/44; C07C209/48; C07C213/00; C07C213/08; C07C231/00; C07C231/06; C07C25/00; C07C25/02; C07C25/13; C07C253/00; C07C253/30; C07C269/00; C07C45/00; C07C45/44; C07C45/61; C07C45/63; C07C51/00; C07C51/08; C07C51/58; C07C51/60; C07C67/00; C07C67/30; C07C67/307; C07D295/00; C07D295/16; C07D295/18; C07D295/182; C07D295/192
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
134 words
Process for preparing an organic compound of the formula wherein R is H, lower alkyl or phenyl and X is a group capable of reacting with MoF 6 and selected from Lewis bases and groups possessing labile hydrogen atoms, by fluorinating a starting compound of the formula ##STR64## wherein Y is a group incapable of reacting with MoF 6 under the following conditions, but is capable of conversion to X by conventional synthesis, comprising reacting substantially anhydrous MoF 6 with said compound ##STR65## under anhydrous conditions in solution in an organic solvent inert with respect to the reactants at a temperature of about -20° C. to about +40° C. under an inert atmosphere to obtain the intermediate product ##STR66## reacting said intermediate product using a conventional organic synthesis to obtain said organic compound ##STR67##
Claim 2
Dependent Claim
134 words
Process for preparing an organic compound of the formula wherein R is H, lower alkyl or phenyl and X is a group capable of reacting with MoF 6 and selected from Lewis bases and groups possessing labile hydrogen atoms, by fluorinating a starting compound of the formula ##STR64## wherein Y is a group incapable of reacting with MoF 6 under the following conditions, but is capable of conversion to X by conventional synthesis, comprising reacting substantially anhydrous MoF 6 with said compound ##STR65## under anhydrous conditions in solution in an organic solvent inert with respect to the reactants at a temperature of about -20° C. to about +40° C. under an inert atmosphere to obtain the intermediate product ##STR66## reacting said intermediate product using a conventional organic synthesis to obtain said organic compound ##STR67##
Claim 3
Dependent Claim
31 words
A process in accordance with claim 1 wherein Y is CN and said conventional organic synthesis comprises alkaline hydrolysis to obtain said organic compound wherein X is --CONH 2 or --COOH.
Claim 4
Dependent Claim
38 words
A process in accordance with claim 2 wherein Y is CN and said conventional organic synthesis comprises total alkaline hydrolysis, followed by acidification, followed by reaction with thionyl chloride to obtain said organic compound wherein X is --COCl.
Claim 5
Dependent Claim
38 words
A process in accordance with claim 1 or 3 wherein X is a --CONR' 2 group (where R' is an alkyl or aryl radical) comprising reacting the corresponding acid chloride (X=--COCl) with a secondary amine (R' 2 NH).
Claim 6
Dependent Claim
52 words
A process in accordance with claim 1 wherein X is a --CHO group and R is a lower alkyl or phenyl group, comprising reacting the corresponding compound in the formula of which X is a --CN group with the aluminum hydride LiAlH(OC 2 H 5 ) 3 and hydrolyzing the resulting mixture.
Claim 7
Dependent Claim
49 words
A process in accordance with claim 1 wherein R is a lower alkyl or phenyl radical and X is a --NHCOOR' group (where R' is an alkyl or aryl radical), comprising reacting the corresponding amide compound (X=--CONH 2 ) with bromine and a R'OH alcohol in alkaline alcoholate medium.
Claim 8
Dependent Claim
45 words
A process in accordance with claim 1 wherein R is hydrogen or a lower alkyl or phenyl group and X is a --CH 2 OH group, comprising reacting the corresponding compound in the formula of which X is the --COOH group with LiAlH 4 .
Claim 9
Dependent Claim
55 words
A process in accordance with claim 1 wherein R is hydrogen or a lower alkyl or phenyl group and X is a --COO(CH 2 ) n NR' 2 group (n being 2 or 3 and R' an alkyl or aryl radical), comprising reacting the corresponding carboxylic compound with Cl(CH 2 ) n NR' 2 .
Claim 10
Dependent Claim
37 words
A process in accordance with claim 1 wherein R is hydrogen or a lower alkyl or phenyl group and X is a --CH 2 NH 2 group comprising reacting the corresponding cyanated compound with LiAlH 4 .
References Cited (Backward Citations)
US2862974A
Cited
US3812177A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-11-05 | 1983-05-07 | 1983-11-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-11-05 | 1987-05-07 | 1987-11-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-11-05 | 1991-05-07 | 1991-11-06 | $7700.00 | Window Closed / Lapsed |