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US4384135A
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Preparation of fluorine-containing diphenyl ethers
Assignee: Syngenta Ltd
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Filing: 1981-01-19
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Granted: 1983-05-17
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Expires: 2001-01-19
Abstract
Abstract A method of preparing a diphenyl ether compound of the formula (II) <IMAGE> (II) wherein X is F, Cl or Br; Z is hydrogen, halogen, NO2 of CN; and W is methyl, cyano, CH3CO-, or a group -C-OR, wherein R is -OH; -OM wherein M is a cation; OR1 wherein R1 is an optionally substituted aliphatic radical; -NR2R3 wherein R2 and R3 are each hydrogen or an optionally substituted aliphatic radical; or -NHSO2R4 wherein R4 is alkyl of 1 to 6 carbon atoms, which comprises reacting a 3-X-substituted-4,5-difluorobenzotrifluoride with a salt of a 3,4-W,Z-substituted phenol. The invention further comprises novel 3-X-4,5-difluorobenzotrifluorides for use in the process.
Inventors
- 👤 David Cartwright
- 👤 Roger Salmon
- 👤 Alfred G. Williams
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 02:32
CPC Classifications
C; C07; C07C; C07C201/00; C07C201/06; C07C201/08; C07C17/00; C07C17/093; C07C17/20; C07C17/202; C07C17/208; C07C17/38; C07C17/383; C07C201/12; C07C209/00; C07C209/30; C07C209/32; C07C209/36; C07C209/365; C07C209/68; C07C209/74; C07C25/00; C07C25/02; C07C25/13; C07C311/00; C07C311/01; C07C311/02; C07C311/03
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
149 words
A process of preparing compounds of the formula (II) ##STR13## wherein X is fluorine, chlorine or bromine, Z is hydrogen, fluorine, chlorine, bromine, iodine, nitro, or cyano, and W is a methyl group, a cyano group, an acetyl group, or a group ##STR14## wherein R is OH; OM wherein M is a cation; OR 1 wherein R 1 is an optionally substituted aliphatic radical; --NR 2 R 3 wherein R 2 and R 3 are each hydrogen or an optionally substituted aliphatic radical; or --NHSO 2 R 4 wherein R 4 is an alkyl radical of 1 to 6 carbon atoms, which comprises reacting a 3-X-substituted-4,5-difluorobenzotrifluoride with a salt of a 3,4-W,Z-substituted phenol in a solvent or diluent for the reactants, and in the case when W is --CO 2 H or --CONHSO 2 R 4 acidifying the product of the reaction, and recovering the compound of formula (II).
Claim 2
Dependent Claim
149 words
A process of preparing compounds of the formula (II) ##STR13## wherein X is fluorine, chlorine or bromine, Z is hydrogen, fluorine, chlorine, bromine, iodine, nitro, or cyano, and W is a methyl group, a cyano group, an acetyl group, or a group ##STR14## wherein R is OH; OM wherein M is a cation; OR 1 wherein R 1 is an optionally substituted aliphatic radical; --NR 2 R 3 wherein R 2 and R 3 are each hydrogen or an optionally substituted aliphatic radical; or --NHSO 2 R 4 wherein R 4 is an alkyl radical of 1 to 6 carbon atoms, which comprises reacting a 3-X-substituted-4,5-difluorobenzotrifluoride with a salt of a 3,4-W,Z-substituted phenol in a solvent or diluent for the reactants, and in the case when W is --CO 2 H or --CONHSO 2 R 4 acidifying the product of the reaction, and recovering the compound of formula (II).
Claim 3
Dependent Claim
33 words
A process as claimed in claim 1 wherein X is chlorine or fluorine, W is a --CO 2 H or --CONHSO 2 R 4 group and Z is chlorine or a nitro group.
Claim 4
Dependent Claim
14 words
A benzotrifluoride compound of the formula ##STR15## wherein X is fluorine, chlorine or bromine.
Claim 5
Dependent Claim
14 words
A benzotrifluoride compound of the formula ##STR15## wherein X is fluorine, chlorine or bromine.
Claim 6
Dependent Claim
64 words
A process of preparing a 3-halogeno-4,5-difluorobenzotrifluoride of the formula defined in claim 3 which comprises reacting a 3,4,5-trihalogenobenzotrifluoride of the formula ##STR16## wherein X is fluorine, chlorine or bromine and Y is fluorine or chlorine provided that X and Y are not both fluorine with an alkali metal fluoride at a temperature of at least 130° C. and separating the desired 3-halogeno-4,5-difluorobenzotrifluoride by distillation.
Claim 7
Dependent Claim
20 words
A process as claimed in claim 4 wherein 3-chloro-4,5-difluorobenzotrifluoride is prepared by reaction of 3,4,5-trichlorobenzotrifluoride with an alkali metal fluoride.
Claim 8
Dependent Claim
20 words
A process as claimed in claim 4 wherein 3,4,5-trifluorobenzotrifluoride is prepared by reaction of 3,4,5-trichlorobenzotrifluoride with an alkali metal fluoride.
Claim 9
Dependent Claim
29 words
A process of preparing 3,4,5-trifluorobenzotrifluoride which comprises reacting 3-chloro or 3-bromo-4,5-difluorobenzotrifluoride with an alkali metal fluoride at a temperature of at least 130° and separating the 3,4,5-trifluorobenzotrifluoride by distillation.
Claim 10
Dependent Claim
29 words
A process of preparing 3,4,5-trifluorobenzotrifluoride which comprises reacting 3-chloro or 3-bromo-4,5-difluorobenzotrifluoride with an alkali metal fluoride at a temperature of at least 130° and separating the 3,4,5-trifluorobenzotrifluoride by distillation.
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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) | 1986-05-16 | 1986-11-15 | 1987-05-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-05-16 | 1990-11-15 | 1991-05-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-05-16 | 1994-11-15 | 1995-05-17 | $7700.00 | Window Closed / Lapsed |