US4262152A
Expired / Lapsed
US
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Preparation of trifluoromethylphenyl nitrophenylethers
Assignee: Rohm and Haas Co
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Filing: 1979-05-02
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Granted: 1981-04-14
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Expires: 1999-05-02
Abstract
Abstract A process for preparing trifluoromethylphenyl nitro phenylethers which comprises treating a trifluoromethylhalobenzene with a base in a cosolvent system to afford a trifluoromethyl phenolate which may be isolated as its free phenol or reacted with an appropriately substituted halobenzene to afford a diphenylether herbicide or a precursor thereto.
Inventors
- 👤 Wayne O. Johnson
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 16:19
CPC Classifications
C; C07; C07C; C07C37/00; C07C37/01; C07C37/055; C07C201/00; C07C201/06; C07C201/12; C07C205/00; C07C205/27; C07C205/35; C07C205/36; C07C205/38; C07C231/00; C07C231/02; C07C37/64; C07C67/00; C07C67/08
Claims Analysis
Total Claims: 8
Claim 1
Independent Claim
174 words
A process for preparing a compound of the formula ##STR27## wherein X is hydrogen, halo, trifluoromethyl or lower alkyl, X" is halo or trifluoromethyl with the proviso that when X" is halo X is trifluoromethyl, and M is the cation of an alkali metal or alkaline earth metal which comprises treating a compound of the formula ##STR28## wherein X and X" are as defined above and X 2 is halo with an alkali metal or alkaline earth metal hydroxide in a solvent system consisting of a dipolar, aprotic solvent with a dielectric constant in the range of from about 30 to about 70 and a non-nucleophilic hydroxy containing solvent and such system being inert to said base wherein the solvents are employed in the ratio of from about 1 part to about 30 parts of the non-nucleophilic hydroxy solvent to about 100 parts of the dipolar aprotic solvent, at a temperature in the range of from about 60° to about 100° C., and, if desired, converting to the free phenol by treatment with acid.
Claim 2
Dependent Claim
174 words
A process for preparing a compound of the formula ##STR27## wherein X is hydrogen, halo, trifluoromethyl or lower alkyl, X" is halo or trifluoromethyl with the proviso that when X" is halo X is trifluoromethyl, and M is the cation of an alkali metal or alkaline earth metal which comprises treating a compound of the formula ##STR28## wherein X and X" are as defined above and X 2 is halo with an alkali metal or alkaline earth metal hydroxide in a solvent system consisting of a dipolar, aprotic solvent with a dielectric constant in the range of from about 30 to about 70 and a non-nucleophilic hydroxy containing solvent and such system being inert to said base wherein the solvents are employed in the ratio of from about 1 part to about 30 parts of the non-nucleophilic hydroxy solvent to about 100 parts of the dipolar aprotic solvent, at a temperature in the range of from about 60° to about 100° C., and, if desired, converting to the free phenol by treatment with acid.
Claim 3
Dependent Claim
13 words
The process of claim 1 wherein X is chloro, and X" is trifluoromethyl.
Claim 4
Dependent Claim
217 words
The process of claim 2 wherein the non-nucleophilic hydroxy containing solvent is selected from: ##STR29## wherein R, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are the same or different groups selected from hydrogen; straight or branched lower alkyl, substituted or unsubstituted phenyl substituents wherein phenyl substituents may be alkyl, halo, lower alkoxy, a benzyl, and the like; R 8 is lower alkyl; n and n 2 are 0 or 1; n 1 is 0 to 2, n 3 is an integer of from 1 to 10; n 4 is 2 to 4 provided that n 1 is 2 only when n and n 2 are both 0, otherwise the sum of n 1 and n 2 may not simultaneously be greater than 1; when n 3 is greater than 2, the sum of n and n 2 may not simultaneously be greater than 1 and n 1 must be 0; when R 7 is hydrogen, n' must be zero and the sum of n and n 2 must be 1 such that at least 3 of the groups R, R' plus either the pair R 2 and R 3 or the pair R 5 and R 6 must not be hydrogen.
Claim 5
Dependent Claim
17 words
The process of claim 3 where the dipolar aprotic solvent is dimethyl sulfoxide, tetrahydrothiophene-1,1-dioxide or hexamethylphosphorphoric triamide.
Claim 6
Dependent Claim
36 words
The process of claim 3 wherein the solvents are employed in the ratio of from about 5 parts to about 20 parts of the non-nucleophilic hydroxy solvent to about 100 parts of the dipolar, aprotic solvent.
Claim 7
Dependent Claim
13 words
The process of claim 5 wherein the alkali metal hydroxide is potassium hydroxide.
Claim 8
Dependent Claim
13 words
The process of claim 5 wherein the alkali metal hydroxide is sodium hydroxide.
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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) | 1984-04-13 | 1984-10-13 | 1985-04-14 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-04-13 | 1988-10-13 | 1989-04-14 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-04-13 | 1992-10-13 | 1993-04-14 | $7700.00 | Window Closed / Lapsed |