Patent US4157344A successfully refreshed from Google Patents.
US4157344A
Expired / Lapsed
US
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Preparation of aryl trifluoromethyl ethers
Assignee: EIDP Inc
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Filing: 1978-01-16
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Granted: 1979-06-05
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Expires: 1998-01-16
Abstract
Abstract A one-step process for the synthesis of aryl trifluoromethyl ethers by reacting phenol or certain substituted phenols with a perhalomethane and hydrogen fluoride is provided. The compounds produced by the process of this invention are useful intermediates in the production of dyestuffs and pharmaceuticals.
Inventors
- 👤 Andrew E. Feiring
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 09:25
CPC Classifications
C; C07; C07C; C07C41/00; C07C41/01; C07C41/16; C07C201/00; C07C201/06; C07C201/12; C07C213/00; C07C213/06; C07C253/00; C07C253/30; C07C45/00; C07C45/61; C07C45/67; C07C45/68; C07C45/70; C07C45/71
Claims Analysis
Total Claims: 4
Claim 1
Independent Claim
149 words
The process of preparing an aryl trifluoromethyl ether of the general formula: ##STR22## comprising reacting in the temperature range of about 80° to about 175° C. and under sufficient pressure to keep most of the hydrogen fluoride in the liquid state the following: (a) a phenolic compound of the formula ##STR23## wherein, independently, R is H, Cl, F or Br; R 1 is H, Cl, Br, F, NO 2 , NH 2 , CN, CF 3 , alkyl containing 1-4 carbon atoms, phenyl or benzoyl; and R 2 is H, Cl, Br, F, NO 2 , NH 2 , CN, CF 3 , alkyl containing 1-4 carbon atoms, phenyl, benzoyl or OH; and (b) at least an equimolar amount of a perhalomethane selected from the group consisting of CCl 4 , CFCl 3 or CBrCl 3 ; and (c) at least three molar equivalents of substantially anhydrous hydrogen fluoride.
Claim 2
Dependent Claim
149 words
The process of preparing an aryl trifluoromethyl ether of the general formula: ##STR22## comprising reacting in the temperature range of about 80° to about 175° C. and under sufficient pressure to keep most of the hydrogen fluoride in the liquid state the following: (a) a phenolic compound of the formula ##STR23## wherein, independently, R is H, Cl, F or Br; R 1 is H, Cl, Br, F, NO 2 , NH 2 , CN, CF 3 , alkyl containing 1-4 carbon atoms, phenyl or benzoyl; and R 2 is H, Cl, Br, F, NO 2 , NH 2 , CN, CF 3 , alkyl containing 1-4 carbon atoms, phenyl, benzoyl or OH; and (b) at least an equimolar amount of a perhalomethane selected from the group consisting of CCl 4 , CFCl 3 or CBrCl 3 ; and (c) at least three molar equivalents of substantially anhydrous hydrogen fluoride.
Claim 3
Dependent Claim
60 words
The process of claim 1 wherein (a) the phenolic compound is reacted with (b) the perhalomethane being present in an amount 2-3 moles per mole of phenolic compound, and (c) from 20-45 moles of substantially anhydrous hydrogen fluoride per mole of phenolic compound, the reaction being carried out in the temperature range of 125° to 150° C. under autogenous pressure.
Claim 4
Dependent Claim
27 words
The process of claim 2 wherein said phenolic compound is selected from the group 3-nitrophenol, 4-nitrophenol, 4-chlorophenol, 4-aminophenol, or 2,4-dichlorophenol and the perhalomethane is CCl 4 .
References Cited (Backward Citations)
GB765527A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-06-04 | 1982-12-04 | 1983-06-05 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-06-04 | 1986-12-04 | 1987-06-05 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-06-04 | 1990-12-04 | 1991-06-05 | $7700.00 | Window Closed / Lapsed |