CN112812035B - Fluoroacetaldehyde-oxygen-aryl oxime compound and synthesis method thereof - Google Patents
Fluoroacetaldehyde-oxygen-aryl oxime compound and synthesis method thereof Download PDFInfo
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- C07C249/04—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes
- C07C249/08—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes by reaction of hydroxylamines with carbonyl compounds
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- C07C251/50—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals
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Abstract
The invention belongs to the technical field of organic fluorine chemical synthesis, and relates to a fluoroacetal-oxygen-aryl oxime compound and a synthesis method thereof. The prepared fluoroacetal-oxygen-aryl oxime compound is a white solid or liquid, has good thermal stability, is not easy to absorb moisture, has no corrosiveness, is convenient to store and transport, is convenient to use in air, has easily obtained reaction raw materials, and can be used as a precursor of fluoroacetonitrile. The method realizes synthesis of tens of grams and has potential for further industrial application.
Description
Technical Field
The invention belongs to the technical field of chemical synthesis of organic fluorine, and particularly relates to a fluoroacetal-oxygen-aryl oxime compound and a synthesis method thereof.
Background
The fluoroacetonitrile is a synthon for synthesizing fluorine-containing heterocyclic compounds, such as trifluoroacetonitrile, is used as an electrophilic reagent for synthesizing trifluoromethyl-containing heterocyclic compounds, and has important application in the fields of pesticides, medicines and the like. However, the trifluoroacetonitrile is a gas with low boiling point (-64 ℃ to-65 ℃) and high toxicity, is not easy to prepare and store, and is difficult to perform experimental operation in a common laboratory. Therefore, it is necessary to develop a safe, easy to handle reagent that generates trifluoroacetonitrile in situ.
The invention reports a method for synthesizing a fluoroacetaldehyde-oxygen-aryl oxime compound by using an easily obtained and easily prepared aryl hydroxylamine and a fluoroalkyl acetaldehyde water (alcohol) compound as raw materials and reacting under an acidic condition, wherein the aryl hydroxylamine and the fluoroalkyl acetaldehyde water (alcohol) compound can be used as a precursor of fluoroacetonitrile.
Disclosure of Invention
The prepared fluoroacetal-oxygen-aryl oxime compound is white solid or liquid, has good thermal stability, is not easy to absorb moisture, has no corrosivity, is convenient to store, transport and use in the air, has easily obtained reaction raw materials, and can be used as a precursor of fluoroacetonitrile.
In order to achieve the purpose, the invention adopts the following technical scheme:
a fluoroacetal-O-aryloxime compound having any one of the following formulae 1 to 8:
a synthetic method of a fluoroacetal-oxygen-aryl oxime compound takes aryl hydroxylamine and fluoroalkyl acetaldehyde water (alcohol) compound as raw materials, and the fluoroacetal-oxygen-aryl oxime compound is obtained by reaction under acidic conditions.
Further, the molar ratio of aryl hydroxylamine to fluoroalkyl acetaldehyde hydrate is (0.5-2) to (1-4).
Furthermore, aryl hydroxylamine and fluoroalkyl acetaldehyde water (alcohol) compound are used as raw materials, and the fluoroacetal-oxygen-aryl oxime compound is obtained under an acidic condition, and the reaction formula is as follows:
further, the aryl hydroxylamine is any one of the following formulas 1 to 4:
further, the fluoroalkylacetaldehyde water (alcohol) hydrate is any one of the following formulas 1 to 2:
further, the synthetic method of the fluoroacetaldehyde-oxygen-aryl oxime compound comprises the following specific steps: in the air atmosphere, putting aryl hydroxylamine compound and fluoroalkyl acetaldehyde water (alcohol) compound into a reactor with a magnetic stirrer, heating to 40-80 ℃ under an acidic condition, stirring for reaction for 24h, cooling to room temperature, extracting with ethyl acetate/water for three times, combining organic phases, removing the solvent by rotary evaporation, and purifying through a silica gel column to obtain the fluoroacetal-oxygen-aryl oxime compound.
The invention has the beneficial effects that:
the invention takes simple and easily obtained aryl hydroxylamine and fluoroalkyl acetaldehyde water (alcohol) compound as raw materials to synthesize the fluoroacetal-oxygen-aryl oxime compound by one step under the acidic condition. The prepared fluoroacetal-oxygen-aryl oxime compound is a white solid or liquid, has good thermal stability, is not easy to absorb moisture, has no corrosiveness, is convenient to store, transport and use in the air, has cheap and easily available reaction raw materials, and can be used as a precursor of fluoroacetonitrile.
Detailed Description
In order to make the present invention more comprehensible, the technical solutions of the present invention are further described below with reference to specific embodiments, but the present invention is not limited thereto.
Example 1
Putting a polytetrafluoroethylene magnet into a 5 mL reaction tube in air atmosphere, adding 0.2 mmol of 2, 4-dinitrophenylhydroxylamine (formula 1) and 0.8 mmol of trifluoroacetic aldehyde hydrate, heating to 40 ℃ under acidic condition, stirring for reaction for 24h, cooling to room temperature, extracting with ethyl acetate/water for three times, combining organic phases, and removing the organic solvent by rotary evaporation; the crude product obtained was subjected to silica gel column chromatography using ethyl acetate/petroleum ether as eluent to give 2,2, 2-trifluoroacetaldehyde-oxy- (2, 4-dinitrophenyl) oxime (isolated yield 67%).1H NMR (400 MHz, CDCl3) δ 8.87 (d, J = 2.7 Hz, 1H), 8.50 (dd, J = 9.3, 2.7 Hz, 1H), 8.11 (q, J = 3.9 Hz, 1H), 7.92 (d, J = 9.3 Hz, 1H). 13C NMR (101 MHz, CDCl3) δ 155.18 (s), 145.46 (q, J = 38.9 Hz), 142.69 (s), 136.68 (s), 129.39 (s), 122.01 (s), 118.75 (q, J = 272.8 Hz), 117.49 (s). 19F NMR (376 MHz, CDCl3) δ -66.64 (d, J= 3.9 Hz). melting point 65.1-66.5 ℃.
Example 2
Putting a polytetrafluoroethylene magnet into a 5 mL reaction tube in air atmosphere, adding 0.2 mmol of 2, 4-dinitrophenylhydroxylamine (formula 1) and 0.8 mmol of trifluoroacetic aldehyde hydrate, heating to 50 ℃ under acidic condition, stirring for reaction for 24h, cooling to room temperature, extracting with ethyl acetate/water for three times, combining organic phases, and removing the organic solvent by rotary evaporation; the crude product obtained was subjected to silica gel column chromatography using ethyl acetate/petroleum ether as eluent to give 2,2, 2-trifluoroacetaldehyde-oxy- (2, 4-dinitrophenyl) oxime (yield 50%). NMR data are given in example 1.
Example 3
Putting a polytetrafluoroethylene magnet into a 5 mL reaction tube in air atmosphere, adding 0.2 mmol of 2, 4-dinitrophenylhydroxylamine (formula 1) and 0.8 mmol of trifluoroacetic aldehyde hydrate, heating to 60 ℃ under acidic condition, stirring for reaction for 24h, cooling to room temperature, extracting with ethyl acetate/water for three times, combining organic phases, and removing the organic solvent by rotary evaporation; the crude product obtained was subjected to silica gel column chromatography using ethyl acetate/petroleum ether as eluent to give 2,2, 2-trifluoroacetaldehyde-oxy- (2, 4-dinitrophenyl) oxime (yield 54%). NMR data are given in example 1.
Example 4
Putting a polytetrafluoroethylene magnet into a 5 mL reaction tube in air atmosphere, adding 0.2 mmol of 2, 4-dinitrophenylhydroxylamine (formula 1) and 0.8 mmol of trifluoroacetic aldehyde hydrate, heating to 70 ℃ under acidic condition, stirring for reaction for 24h, cooling to room temperature, extracting with ethyl acetate/water for three times, combining organic phases, and removing the organic solvent by rotary evaporation; the crude product obtained was subjected to silica gel column chromatography using ethyl acetate/petroleum ether as eluent to give 2,2, 2-trifluoroacetaldehyde-oxy- (2, 4-dinitrophenyl) oxime (yield 50%). NMR data are given in example 1.
Example 5
Putting a polytetrafluoroethylene magnet into a 5 mL reaction tube in air atmosphere, adding 0.2 mmol of 2, 4-dinitrophenylhydroxylamine (formula 1) and 0.8 mmol of trifluoroacetic aldehyde hydrate, heating to 80 ℃ under acidic condition, stirring for reaction for 24h, cooling to room temperature, extracting with ethyl acetate/water for three times, combining organic phases, and removing the organic solvent by rotary evaporation; the crude product obtained was subjected to silica gel column chromatography using ethyl acetate/petroleum ether as eluent to give 2,2, 2-trifluoroacetaldehyde-oxy- (2, 4-dinitrophenyl) oxime (yield 35%). NMR data are given in example 1.
Example 6
Putting a polytetrafluoroethylene magnet into a 5 mL reaction tube in air atmosphere, adding 0.2 mmol of 2-nitrophenylhydroxylamine (formula 3) and 0.8 mmol of trifluoro acetaldehyde hydrate, heating to 60 ℃ under an acidic condition, stirring for reaction for 24 hours, cooling to room temperature, extracting with ethyl acetate/water for three times, combining organic phases, and removing an organic solvent by rotary evaporation; the crude product obtained was subjected to silica gel column chromatography using ethyl acetate/petroleum ether as eluent to give 2,2, 2-trifluoroacetaldehyde-oxy- (2-nitrophenyl) oxime (isolated yield 67%).1H NMR (400 MHz, CDCl3) δ 7.98 (m, 2H), 7.67 (d, J = 8.3 Hz, 1H), 7.63 (t, J = 7.8 Hz, 1H), 7.25 (t, J = 7.6 Hz, 1H). 13C NMR (101 MHz, CDCl3) δ 151.37 (s), 143.36 (q, J = 38.4 Hz), 134.80 (s), 125.77 (s), 124.06 (s), 119.23 (q, J = 272.1 Hz), 117.50 (s). 19F NMR (376 MHz, CDCl3) δ -66.59 (d, J = 3.8 Hz).
Example 7
Placing a polytetrafluoroethylene magnet particle in a 5 mL reaction tube in air atmosphere, adding 0.2 mmol 4-nitrophenylhydroxylamine (formula 2) and 0.8 mmol trifluoroacetic aldehyde hydrate, heating at 60 deg.C under acidic condition, stirring for reaction for 24h, cooling to room temperature, extracting with ethyl acetate/water for three times, combining organic phases, and rotary evaporatingRemoving the organic solvent; the crude product obtained was subjected to silica gel column chromatography using ethyl acetate/petroleum ether as eluent to give 2,2, 2-trifluoroacetaldehyde-oxy- (4-nitrophenyl) oxime (isolated yield 67%).1H NMR (400 MHz, CDCl3) δ 8.27 (d, J = 9.2 Hz, 2H), 7.90 (q, J = 3.9 Hz, 1H), 7.34 (d, J = 9.2 Hz, 2H). 13C NMR (101 MHz, CDCl3) δ 162.45 (s), 143.99 (s), 142.59 (q, J = 38.4 Hz), 125.93 (d, J = 5.7 Hz), 119.27 (q, J = 272.0 Hz), 114.76 (s). 19F NMR (376 MHz, CDCl3) δ -66.58 (d, J = 3.9 Hz).
Example 8
Putting a polytetrafluoroethylene magnet into a 5 mL reaction tube in air atmosphere, adding 0.2 mmol of 4-cyanophenylhydroxylamine (formula 4) and 0.6 mmol of trifluoroacetic aldehyde hydrate, heating to 60 ℃ under acidic condition, stirring for reaction for 24h, cooling to room temperature, extracting with ethyl acetate/water for three times, combining organic phases, and removing the organic solvent by rotary evaporation; the crude product obtained was subjected to silica gel column chromatography using ethyl acetate/petroleum ether as eluent to give 2,2, 2-trifluoroacetaldehyde-oxy- (4-cyanophenyl) oxime (yield 74%).1H NMR (400 MHz, CDCl3) δ 7.87 (q, 3.7 Hz, 1H), 7.67 (d, J = 8.5 Hz, 2H), 7.31 (d, J = 8.5 Hz, 2H). 13C NMR (101 MHz, CDCl3) δ 161.04 (s), 142.19 (q, J = 38.3 Hz), 134.17 (s), 119.31 (q, 266.7 Hz), 118.58 (s), 115.28 (s), 107.61 (s). 19F NMR (376 MHz, CDCl3) δ -66.60 (d, J= 3.7 Hz) melting point 62.1-63.3 ℃.
Example 9
Placing a polytetrafluoroethylene magnet into a 5 mL reaction tube in an air atmosphere, adding 0.2 mmol of 2, 4-dinitrophenylhydroxylamine (formula 1) and 0.6 mmol of difluoroacetaldehyde hemiethanol, heating to 50 ℃ under an acidic condition, stirring for reaction for 24 hours, cooling to room temperature, extracting with ethyl acetate/water for three times, combining organic phases, and removing the organic solvent by rotary evaporation; the crude product obtained is chromatographed on silica gel using ethyl acetate/petroleum ether as eluent to give 2, 2-difluoroacetaldehyde-oxy- (2, 4-dinitrophenyl) oxime (yield 5)4%）。1H NMR (400 MHz, CDCl3) δ 8.87 (d, J = 2.6 Hz, 1H), 8.48 (dd, J = 9.3, 2.7 Hz, 1H), 8.05 (dt, J = 6.5, 3.5 Hz, 1H), 7.88 (d, J = 9.3 Hz, 1H), 6.36 (td, J = 53.4, 6.0 Hz, 1H). 13C NMR (101 MHz, CDCl3) δ 155.65 (s), 150.17 (t, J = 32.7 Hz), 142.43 (s), 136.75 (s), 129.41 (s), 122.16 (s), 117.43 (s), 110.25 (t, J = 238.7 Hz). 19F NMR (376 MHz, CDCl3) δ -117.89 (dd, J= 53.4, 3.5 Hz). melting point 53.0-54.8 ℃.
Example 10
Placing a polytetrafluoroethylene magnet particle in a 5 mL reaction tube in the air atmosphere, adding 0.2 mmol of 4-nitrophenylhydroxylamine (formula 2) and 0.6 mmol of difluoroacetaldehyde hemiethanol, heating to 50 ℃ under an acidic condition, stirring for reaction for 24 hours, cooling to room temperature, extracting with ethyl acetate/water for three times, combining organic phases, and removing the organic solvent by rotary evaporation; the crude product obtained was subjected to silica gel column chromatography using ethyl acetate/petroleum ether as eluent to give 2, 2-difluoroacetaldehyde-oxy- (4-nitrophenyl) oxime (yield 93%).1H NMR (400 MHz, CDCl3) δ 8.24 (m, 2H), 7.85 (dt, J = 6.5, 3.4 Hz, 1H), 7.29 (m, 2H), 6.33 (td, J = 53.7, 6.2 Hz, 1H). 13C NMR (101 MHz, CDCl3) δ 162.74 (s), 147.34 (t, J = 32.7 Hz), 143.67 (s), 125.92 (s), 114.62 (s, J = 12.8 Hz), 110.96 (t, J = 236.9 Hz).19F NMR (376 MHz, CDCl3) δ -117.38 (dd, J = 53.7, 3.3 Hz).
Example 11
Placing a polytetrafluoroethylene magnet particle in a 5 mL reaction tube in air atmosphere, adding 0.2 mmol of 2-nitrophenylhydroxylamine (formula 3) and 0.6 mmol of difluoroacetaldehyde hemiethanol, heating to 50 ℃ under an acidic condition, stirring for reaction for 24 hours, cooling to room temperature, extracting with ethyl acetate/water for three times, combining organic phases, and removing the organic solvent by rotary evaporation; the crude product obtained is chromatographed on silica gel using ethyl acetate/petroleum ether as eluent to give 2, 2-difluoroacetaldehyde-oxy- (2-nitrophenyl) oxime (yield 9)0%）。1H NMR (400 MHz, CDCl3) δ 7.94 (m, 2H), 7.61 (m, 2H), 7.21 (ddd, J = 8.5, 6.7, 2.0 Hz, 1H), 6.31 (td, J = 53.7, 6.2 Hz, 1H). 13C NMR (101 MHz, CDCl3) δ 151.47 (s), 147.92 (t, J = 32.6 Hz), 134.51 (s), 125.58 (s), 123.47 (s), 117.30 (s), 110.74 (t, J = 237.3 Hz). 19F NMR (376 MHz, CDCl3) δ -117.51 (dd, J = 53.6, 3.4 Hz).
Example 12
Placing a polytetrafluoroethylene magnet particle in a 5 mL reaction tube in an air atmosphere, adding 0.2 mmol of 4-cyanophenylhydroxylamine (formula 4) and 0.6 mmol of difluoroacetaldehyde hemiethanol, heating to 50 ℃ under an acidic condition, stirring for reaction for 24 hours, cooling to room temperature, extracting with ethyl acetate/water for three times, combining organic phases, and removing the organic solvent by rotary evaporation; the crude product obtained was subjected to silica gel column chromatography using ethyl acetate/petroleum ether as eluent to give 2, 2-difluoroacetaldehyde-oxy- (4-cyanophenyl) oxime (yield 89%).1H NMR (400 MHz, CDCl3) δ 7.83 (dt, J = 6.5, 3.3 Hz, 1H), 7.65 (m, 2H), 7.28 (m, 2H), 6.31 (td, J = 53.7, 6.3 Hz, 1H). 13C NMR (101 MHz, CDCl3) δ 161.30 (s), 146.96 (t, J = 32.7 Hz), 134.14 (s), 118.73 (s), 115.21 (s), 111.03 (t, J = 236.8 Hz), 107.15 (s).19F NMR (376 MHz, CDCl3) δ -117.29 (dd, J= 53.8, 3.4 Hz).
Reaction steps for preparing trifluoroacetonitrile:
a5 mL reaction tube is filled with a Teflon magnet, 0.2 mmol of 2,2, 2-trifluoroacetaldehyde-oxy- (2, 4-dinitrophenyl) oxime is added, a certain amount of base (such as triethylamine, cesium carbonate and potassium tert-butoxide) is added, and after stirring, trifluoroacetonitrile is generated (nuclear magnetic yield > 99%).
The above description is only a preferred embodiment of the present invention, and all the equivalent changes and modifications made according to the claims of the present invention should be covered by the present invention.
Claims (3)
1. A fluoroacetal-oxo-aryl oxime compound characterized by: the fluoro acetaldehyde-oxygen-aryl oxime compound is any one of the following formulas 1 to 8:
2. the method for synthesizing fluoroacetal-oxo-aryl oximes according to claim 1, characterized in that: aryl hydroxylamine and fluoroalkyl acetaldehyde compound are used as raw materials to synthesize fluoro acetaldehyde-oxygen-aryl oxime compound under acidic condition; the molar ratio of the aryl hydroxylamine to the fluoroalkyl acetaldehyde compound is (0.5-2) to (1-4);
the aryl hydroxylamine is any one of the following formulas 1 to 4:
the fluoroalkyl acetaldehyde compound is any one of the following formulas 1 to 2:
the reaction temperature is 40-80 ℃; the reaction time was 24 h.
3. The method for synthesizing fluoroacetal-oxo-aryl oximes according to claim 2, characterized in that: the specific synthesis steps are as follows: in the air atmosphere, putting aryl hydroxylamine compound and fluoroalkyl acetaldehyde compound into a reactor with a magnetic stirring bar, and reacting under the acidic condition to obtain the fluoroacetal-oxygen-aryl oxime compound.
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| DE3036281A1 (en) * | 1980-09-26 | 1982-05-13 | Boehringer Mannheim Gmbh, 6800 Mannheim | 0-SUBSTITUTED PETROLEUM ACID OXIMES, METHOD FOR THE PRODUCTION THEREOF, THEIR USE AND MEDICINAL PRODUCTS CONTAINING THESE COMPOUNDS |
| CN1882323A (en) * | 2003-09-25 | 2006-12-20 | 惠氏公司 | Substituted benzofuran oximes |
| WO2010065579A2 (en) * | 2008-12-02 | 2010-06-10 | E. I. Du Pont De Nemours And Company | Fungicidal heterocyclic compounds |
| CN102746190A (en) * | 2012-08-02 | 2012-10-24 | 江苏泰特尔化工有限公司 | Preparation method of trifluoroacetonitrile |
| JP7035047B2 (en) * | 2016-11-28 | 2022-03-14 | 住友化学株式会社 | Tetrazolinone compounds and their uses |
| CN108033928B (en) * | 2018-02-01 | 2019-06-04 | 福州大学 | A method of synthesis 2- trifluoromethyl oxazoline compound |
| CN110642748B (en) * | 2019-09-20 | 2023-03-31 | 华南理工大学 | O- (2-trifluoromethyl-2-hydroxyethyl) oxime ether derivative and synthetic method and application thereof |
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