US4469893A
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Method for the preparation of nitrodiphenyl ethers
Assignee: Occidental Chemical Corp
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Filing: 1982-03-22
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Granted: 1984-09-04
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Expires: 2002-03-22
Abstract
Abstract Diphenyl esters of the formula ##STR1## wherein R is hydrogen, carboxy, carboxylate salt or ester, formyl, cyano, alkyl, alkoxy, chloro, bromo, or N, N-dialkyl amino, are prepared by reacting a chloro-fluoro-benzotrifluoride with a nitro-phenoxide of the formula ##STR2## where R is defined above, and M is a cation of an alkali metal or an alkaline earth metal.
Inventors
- 👤 David Y. Tang
- 👤 Byron R. Cotter
- 👤 Frederick J. Goetz
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 12:36
CPC Classifications
C; C07; C07C; C07C201/00; C07C201/06; C07C201/12; C07C17/00; C07C17/093; C07C201/08
Claims Analysis
Total Claims: 33
Claim 1
Independent Claim
106 words
A process for the preparation of diphenyl ethers of the formula ##STR7## wherein n is 1 or 2, R is hydrogen; formyl; cyano; alkyl, of 1-6 carbon atoms; alkoxy, of 1-6 carbon atoms; chloro; bromo; N, N-dialkyl amino, the alkyl group being preferably 1-4 carbon atoms; carboxyl, carboxylate salts; or carboxylate esters of the formula CO 2 R' wherein R' is alkyl of 1-6 carbon atoms, which comprises reacting a chlorofluorobenzotrifluoride of the formula ##STR8## where n is defined above, with a nitro-phenoxide of the formula ##STR9## where R is defined above, and M is a cation of an alkali metal or an alkaline earth metal.
Claim 2
Dependent Claim
106 words
A process for the preparation of diphenyl ethers of the formula ##STR7## wherein n is 1 or 2, R is hydrogen; formyl; cyano; alkyl, of 1-6 carbon atoms; alkoxy, of 1-6 carbon atoms; chloro; bromo; N, N-dialkyl amino, the alkyl group being preferably 1-4 carbon atoms; carboxyl, carboxylate salts; or carboxylate esters of the formula CO 2 R' wherein R' is alkyl of 1-6 carbon atoms, which comprises reacting a chlorofluorobenzotrifluoride of the formula ##STR8## where n is defined above, with a nitro-phenoxide of the formula ##STR9## where R is defined above, and M is a cation of an alkali metal or an alkaline earth metal.
Claim 3
Dependent Claim
11 words
A process according to claim 1 wherein the chloro-fluorobenzotrifluoride is 3-chloro-4-fluorobenzotrifluoride.
Claim 4
Dependent Claim
11 words
A process according to claim 1 wherein the chloro-fluorobenzotrifluoride is 2-chloro-5-fluorobenzotrifluoride.
Claim 5
Dependent Claim
11 words
A process according to claim 1 wherein the chlorofluorobenzotrifluoride is 5-chloro-2-fluorobenzotrifluoride.
Claim 6
Dependent Claim
11 words
A process according to claim 1 wherein the chlorofluorobenzotrifluoride is 2,5-dichloro-4-fluorobenzotrifluoride.
Claim 7
Dependent Claim
13 words
A process according to claim 1, carried out in a dipolar aprotic solvent.
Claim 8
Dependent Claim
15 words
A process according to claim 6 wherein M is a cation of an alkali metal.
Claim 9
Dependent Claim
10 words
A process according to claim 7 wherein R is hydrogen.
Claim 10
Dependent Claim
13 words
A process according to claim 7 wherein R is an alkali metal carboxylate.
Claim 11
Dependent Claim
10 words
A process according to claim 7 wherein R is formyl.
Claim 12
Dependent Claim
18 words
A process according to claim 7 carried out at a temperature of about 50° to about 300° Celsius.
Claim 13
Dependent Claim
11 words
A process according to claim 11 carried out at autogenous pressure.
Claim 14
Dependent Claim
11 words
A process according to claim 11 carried out at atmospheric pressures.
Claim 15
Dependent Claim
27 words
A process for the preparation of 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzoic acid which comprises reacting 3-chloro-4-fluorobenzotrifluoride with a di-salt of 5-hydroxy-2-nitrobenzoic acid and acidifying the product with a strong inorganic acid.
Claim 16
Dependent Claim
27 words
A process for the preparation of 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzoic acid which comprises reacting 3-chloro-4-fluorobenzotrifluoride with a di-salt of 5-hydroxy-2-nitrobenzoic acid and acidifying the product with a strong inorganic acid.
Claim 17
Dependent Claim
16 words
A process according to claim 14 wherein the di-salt is the di-potassium salt of 5-hydroxy-2-nitrobenzoic acid.
Claim 18
Dependent Claim
23 words
A process according to claim 15 carried out at about 50° to about 300° Celsius in the presence of a dipolar aprotic solvent.
Claim 19
Dependent Claim
14 words
A process for the preparation of 4-(2-chloro-4-trifluoromethyl-phenoxy)-nitrobenzene which comprises reacting 3-chloro-4-fluorobenzotrifluoride with a 4-nitrophenoxide.
Claim 20
Dependent Claim
14 words
A process for the preparation of 4-(2-chloro-4-trifluoromethyl-phenoxy)-nitrobenzene which comprises reacting 3-chloro-4-fluorobenzotrifluoride with a 4-nitrophenoxide.
Claim 21
Dependent Claim
36 words
A process according to claim 17 wherein the 4-nitrophenoxide is potassium 4-nitrophenoxide and the process is carried out at a temperature of about 50° to about 300° Celsius in the presence of a dipolar aprotic solvent.
Claim 22
Dependent Claim
13 words
A process for the preparation of 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzaldehyde which comprises reacting 3-chloro-4-fluorobenzotrifluoride with 5-hydroxy-2-nitrobenzaldehyde.
Claim 23
Dependent Claim
13 words
A process for the preparation of 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzaldehyde which comprises reacting 3-chloro-4-fluorobenzotrifluoride with 5-hydroxy-2-nitrobenzaldehyde.
Claim 24
Dependent Claim
26 words
A process according to claim 19 carried out at a temperature of about 50° to about 300° Celsius in the presence of a dipolar aprotic solvent.
Claim 25
Dependent Claim
14 words
A process for the preparation of 4-(4-chloro-3-trifluoromethylphenoxy)-nitrobenzene which comprises reacting 2-chloro-5-fluorobenzotrifluoride with a 4-nitrophenoxide.
Claim 26
Dependent Claim
14 words
A process for the preparation of 4-(4-chloro-3-trifluoromethylphenoxy)-nitrobenzene which comprises reacting 2-chloro-5-fluorobenzotrifluoride with a 4-nitrophenoxide.
Claim 27
Dependent Claim
36 words
A process according to claim 21 wherein the 4-nitrophenoxide is potassium 4-nitrophenoxide and the process is carried out at a temperature of about 50° to about 300° Celsius in the presence of a dipolar aprotic solvent.
Claim 28
Dependent Claim
14 words
A process for the preparation of 4-(4-chloro-2-trifluoromethylphenoxy)-nitrobenzene which comprises reacting 5-chloro-2-fluorobenzotrifluoride with a 4-nitrophenoxide.
Claim 29
Dependent Claim
14 words
A process for the preparation of 4-(4-chloro-2-trifluoromethylphenoxy)-nitrobenzene which comprises reacting 5-chloro-2-fluorobenzotrifluoride with a 4-nitrophenoxide.
Claim 30
Dependent Claim
36 words
A process according to claim 23 wherein the 4-nitrophenoxide is potassium 4-nitrophenoxide and the process is carried out at a temperature of about 50° to about 300° Celsius in the presence of a dipolar, aprotic solvent.
Claim 31
Dependent Claim
14 words
A process for the preparation of 4-(2,5-dichloro-4-trifluoromethylphenoxy)-nitrobenzene which comprises reacting 2,5-dichloro-4-fluorobenzotrifluoride with a 4-nitrophenoxide.
Claim 32
Dependent Claim
14 words
A process for the preparation of 4-(2,5-dichloro-4-trifluoromethylphenoxy)-nitrobenzene which comprises reacting 2,5-dichloro-4-fluorobenzotrifluoride with a 4-nitrophenoxide.
Claim 33
Dependent Claim
36 words
A process according to claim 25 wherein the 4-nitrophenoxide is potassium 4-nitrophenoxide and the process is carried out at a temperature of about 50° to about 300° Celsius in the presence of a dipolar, aprotic solvent.
References Cited (Backward Citations)
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1987-09-04 | 1988-03-05 | 1988-09-04 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-09-04 | 1992-03-05 | 1992-09-04 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-09-04 | 1996-03-05 | 1996-09-04 | $7700.00 | Window Closed / Lapsed |