CN106631680A - Method for synthesizing trifluoromethyl aromatic compounds - Google Patents
Method for synthesizing trifluoromethyl aromatic compounds Download PDFInfo
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- CN106631680A CN106631680A CN201611185974.7A CN201611185974A CN106631680A CN 106631680 A CN106631680 A CN 106631680A CN 201611185974 A CN201611185974 A CN 201611185974A CN 106631680 A CN106631680 A CN 106631680A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/32—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by introduction of halogenated alkyl groups into ring compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/22—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of halogens; by substitution of halogen atoms by other halogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/363—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/307—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of halogen; by substitution of halogen atoms by other halogen atoms
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/26—Radicals substituted by halogen atoms or nitro radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
- C07D307/88—Benzo [c] furans; Hydrogenated benzo [c] furans with one oxygen atom directly attached in position 1 or 3
Abstract
The invention aims to provide a method for converting arylamine into trifluoromethyl aromatic compounds under simple conditions. The trifluoromethyl aromatic compounds can be widely applied to the fields of pesticides, medicines, organic materials and the like. The method is characterized by comprising steps of (1), synthesizing Toni reagents alpha from sodium periodate, 2-iodobenzoic acid, acetic anhydride, cesium fluoride and Ruppert reagents; (2), dissolving the arylamine and hydrochloric acid in 1, 2-dichloroethane, stirring the arylamine, the hydrochloric acid and the 1, 2-dichloroethane for 5-10 min to obtain mixtures, adding tert-butyl nitrite into the mixtures under low-temperature conditions, carrying out stirring reaction for 30-60 min to obtain reaction products, adding tetrafluoroboric acid tetra-acetonitrile copper, the Toni reagents alpha and sodium bicarbonate into the reaction products and carrying micro-heat reaction for 10-20 hours; sequentially filtering, washing and drying reaction liquid after reaction is completely carried out and carrying out column chromatography separation and purification on the reaction liquid to obtain target products. The method has the advantage that the trifluoromethyl aromatic compounds can be widely applied to the fields of pesticides, medicines, organic materials and the like.
Description
Technical field
The present invention is a kind of synthetic method of trifluoromethyl aromatic compound.By arylamine cheap and easy to get better simply
Under the conditions of be converted into agricultural chemicals, medicine and the field such as organic material all trifluoromethyl aromatic compounds with extensive use.
Technical background
Trifluoromethyl is prevalent in various bioactive molecules, be generally used for adjust bioavilability, with reference to affine
Power and medicine, the metabolic stability of agricultural chemicals.Trifluoromethyl is introduced into targeting target, nothing with one kind reliable, effective method
It is suspected to be work most noticeable in current fluorine chemistry.However, being limited to effective synthetic method, trifluoromethyl compound is (special
Be not trifluoromethyl fragrance and heteroaromatic compound) extensive application there is limitation.In recent decades, aromatic compound
Notable achievement is had been achieved with the trifluoromethylation of heteroaromatic compound aspect.Developed it is more green, sustainable, cheap and
The wide method of application, the cross-coupling reaction of wherein copper catalysis/promotion is of greatest concern.
Both at home and abroad in the research boom of organic fluorine chemistry, an existing fluoroalkylation, fluoroalkyl and trifluoromethylation
Reaction, there is perfluoroalkylation reaction again.Wherein, the trifluoromethylation reaction of aromatic compound is even more whole fluorine chemistry research
Focus, is primarily due to the aromatic containing trifluoromethyl and has obtained extensively in fields such as agricultural chemicals, medicine and organic materials
Apply generally.
The content of the invention
The present invention is mainly amine source from arylamine cheap and easy to get, and support Buddhist nun's reagent α is trifluoromethyl reagent, in cheap copper
Buddhist nun's reagent α is ask to generate trifluoromethyl free radical (CF in the presence of catalyst3), and then the amino of arylamine is converted into fluoroform
Base, obtains in the fields such as medicine, agricultural chemicals all trifluoromethyl aromatics with important use.
Concrete grammar is first step synthesis support Buddhist nun reagent α, and second step is that under the catalysis of copper, Buddhist nun's reagent α is anti-with arylamine for support
Should, amido is changed into trifluoromethyl by realization.Product passes through the processes such as filtration, alkali cleaning, washing, drying, eventually through column chromatography
Chromatogram obtains trifluoromethyl aromatic compound.
The technical solution used in the present invention is as follows：
A kind of synthetic method of trifluoromethyl aromatic compound, comprises the following steps：
1) with sodium metaperiodate, 2- iodo-benzoic acids, acetic anhydride, cesium fluoride and Ruppert reagents as Material synthesis support Buddhist nun's reagent
α。
2) by arylamine and dissolving with hydrochloric acid in DCE, 5-10min is stirred, nitrous acid special butyl ester is added under cryogenic, stirred
Mix reaction 30-60min, after add the acetonitrile copper of tetrafluoro boric acid four, support Buddhist nun reagent α, sodium acid carbonate, react low-grade fever.Reaction terminates
Filter successively afterwards, wash, be dried and filter, the purification of Jing column chromatography chromatograms obtains target product.
In said method, the support Buddhist nun's reagent α for preparing is light yellow solid, and by nuclear magnetic resonance spectrometer and melting point apparatus
Compound to obtaining is characterized, and product is determined for support Buddhist nun reagent α with document contrast.
In said method, arylamine is 10-20 hours with the reaction time of support Buddhist nun reagent α.
The present invention is a kind of synthetic method of trifluoromethyl aromatic compound, the product can adjust bioavilability,
Binding affinity, especially all has important use in fields such as medicine, agricultural chemicals.
Specific embodiment
It is below the specific embodiment of the present invention.
The synthetic route chart of the embodiment of the present invention, as illustrated, synthetic route is divided into two steps：
The first step, holds in the palm the synthesis of Buddhist nun reagent α：Sodium metaperiodate 7.125g (33.3mmol) and 2- iodobenzene first are accurately weighed first
Sour 7.5g (30.3mmol), in N2Under protection, they are sequentially added in dry 250mL there-necked flasks, add 60mL vinegar
Acid solution (30%aq), is stirred at reflux 4h.After reaction terminates, reactant liquor is poured into beaker and diluted with 120mL cold water, cooling
To room temperature, 1h, collected by suction crude product are stood, and Xian's crude product is drenched with frozen water and acetone.By the solid vavuum pump after drip washing
Drain, obtain compound A (7.774g).Accurately Weigh Compound A 7.774g (52.0mmol) adds dry 100mL round bottoms
In flask, acetic anhydride is added, be heated to reflux (about 15min), to solution in light yellow, stop heating, there is white crystalline substance after cooling
Body is separated out.Refrigerator (- 18 DEG C) is placed reaction liquid into again overnight to crystallize, white crystal is collected by filtration under the conditions of lucifuge, use vacuum oil
Pump drains in crystal, obtains compound B (6.344g).Accurate Weigh Compound B 6.344g (21.0mmol) and cesium fluoride
0.638g (4.2mmol), in N2Under protection, they are sequentially added in dry 50mL reaction tubes, add Ruppert reagents
The mixed liquor of 4.175g (29.0mmol) and acetonitrile, is stirred overnight.After reaction terminates, removal of solvent under reduced pressure, by the solid for obtaining
Column chromatography is carried out, final product (5.590g) is obtained.Its reaction expression formula is Fig. 1.
Second step, the synthesis of trifluoromethyl aromatic compound：Arylamine, hydrochloric acid and nitrous acid special butyl ester are entered at low temperature
Row diazo-reaction, adds the acetonitrile copper of tetrafluoro boric acid four, support Buddhist nun reagent α, NaHCO3And acetonitrile, it is warming up to 40-80 DEG C of reaction
10-20 hours, reaction is filtered successively after terminating, washs, is dried and filtered, and Jing column chromatography chromatogram separating-purifyings obtain final product,
Yield is weighed and calculated, is characterized with nuclear magnetic resonance, its reaction expression formula is Fig. 2.
Description of the drawings：
Fig. 1：The synthesis of support Buddhist nun reagent α
Fig. 2：Synthesis (R=Ph, OCH of trifluoromethyl aromatic compound3, Cl and COOH etc.)
Example one, the synthesis of 4- trifluoromethyl-biphenyls
By 0.084g 4- aminobphenyls add equipped with magnetic stir bar 25ml reaction tubes in, add HCl (0.13g) and
The mixed liquor of DCE, adds 0.062g t-BuONO in reaction tube after reaction 5min, and is placed on stirring reaction in ice salt bath
20min.0.3g support Buddhist nun reagent α are weighed again, and the acetonitrile copper of 0.314g tetrafluoro boric acids four, 0.034g sodium acid carbonates successively add them
Enter reaction tube, the stirring reaction 10-20 hour at 50 DEG C, after reaction terminates, reactant liquor is filtered, washed and dried successively, then Jing
Column chromatography chromatogram separating-purifying obtains colorless solid 0.091g (yield is 82%).
Example two, the synthesis of 4- trifluoromethyl methyl phenyl ethers anisoles
0.061g 4- aminoanisoles are weighed, in adding the 25mL reaction tubes equipped with magnetic stir bar, and HCl is added
(0.13g) with the mixed liquor of DCE, 0.062g t-BuONO are added in reaction tube after reaction 5min, and is placed on ice salt bath
Middle stirring reaction 20min.0.3g support Buddhist nun reagent α, the acetonitrile copper of 0.314g tetrafluoro boric acids four, 0.34g sodium acid carbonates, by it are weighed again
Sequentially add in reaction tube, the stirring reaction 10-20 hour at 25 DEG C, after reaction terminates, reactant liquor filters successively, wash and
It is dried, then Jing column chromatography chromatogram separating-purifyings obtain colourless liquid 0.073g (yield is 83%).
Example three, the synthesis of 1- fluoroform -4- chlorobenzenes
Weigh 0.064g 4- chloroanilines, in adding the 25mL reaction tubes equipped with magnetic stir bar, add HCl (0.13g) and
The mixed liquor of DCE, adds 0.062g t-BuONO in reaction tube after reaction 5min, and is placed on stirring reaction in ice salt bath
20min.0.3g support Buddhist nun reagent α are weighed again, and the acetonitrile copper of 0.314g tetrafluoro boric acids four, 0.034g sodium acid carbonates successively add them
In entering reaction tube, the stirring reaction 10-20 hour at 50 DEG C, after reaction terminates, reactant liquor is filtered, washed and dried successively, then
Jing column chromatography chromatogram separating-purifyings obtain colourless liquid 0.058g (yield is 62%).
Example four, the synthesis of 4- trifluoromethylbenzoic acids
0.069g PABAs are weighed, in adding the 25mL reaction tubes equipped with magnetic stir bar, HCl is added
(0.13g) with the mixed liquor of DCE, 0.062g t-BuONO are added in reaction tube after reaction 5min, and is placed on ice salt bath
Middle stirring reaction 20min.0.3g support Buddhist nun reagent α are weighed again, and the acetonitrile copper of 0.314g tetrafluoro boric acids four, 0.034g sodium acid carbonates are incited somebody to action
They are sequentially added in reaction tube, the stirring reaction 10-20 hour at 50 DEG C, and after reaction terminates, reactant liquor is filtered successively, washed
And drying, then Jing column chromatography chromatogram separating-purifyings obtain white solid 0.068g (yield is 73%).
Example five, the synthesis of 3- trifluoromethyl pyridines
Weigh 0.047g 3- aminopyridines, in entering the 25mL reaction tubes equipped with magnetic stir bar, add HCl (0.13g) and
The mixed liquor of DCE, adds 0.062g t-BuONO in reaction tube after reaction 5min, and is placed on stirring reaction in ice salt bath
20min.0.3g support Buddhist nun reagent α are weighed again, and the acetonitrile copper of 0.314g tetrafluoro boric acids four, 0.034g sodium acid carbonates successively add them
In entering reaction tube, the stirring reaction 10-20 hour at 50 DEG C, after reaction terminates, reactant liquor is filtered, washed and dried successively, then
Jing column chromatography chromatogram separating-purifyings obtain colourless liquid 0.04g (yield is 56%).
Example six, the synthesis of 4- trifluoromethyl acetophenones
0.067g 4- aminoacetophenones are weighed, in entering the 25mL reaction tubes equipped with magnetic stir bar, HCl (0.13g) is added
With the mixed liquor of DCE, 0.062g t-BuONO are added in reaction tube after reaction 5min, and it is anti-to be placed on stirring in ice salt bath
Answer 20min.Weigh again 0.3g support Buddhist nun reagent α, the acetonitrile copper of 0.314g tetrafluoro boric acids four, 0.034g sodium acid carbonates, by them successively
In adding reaction tube, the stirring reaction 10-20 hour at 50 DEG C, after reaction terminates, reactant liquor is filtered, washed and dried successively,
Again Jing column chromatography chromatograms separating-purifying obtains white solid 0.072g (yield is 77%).
Example seven, the synthesis of 2- trifluoromethyl naphthalenes
0.071g 2- naphthylamines is weighed, in entering the 25mL reaction tubes equipped with magnetic stir bar, HCl (0.13g) and DCE is added
Mixed liquor, 0.062g t-BuONO are added in reaction tube after reaction 5min, and be placed on stirring reaction 20 in ice salt bath
min.0.3g support Buddhist nun reagent α are weighed again, and the acetonitrile copper of 0.314g tetrafluoro boric acids four, 0.034g sodium acid carbonates sequentially add them
In reaction tube, the stirring reaction 10-20 hour at 50 DEG C, after reaction terminates, reactant liquor is filtered, washed and dried successively, then Jing
Column chromatography chromatogram separating-purifying obtains white solid 0.087g (yield is 88%).
Example eight, the synthesis of 4- trifluoromethyl benzoic acid methyl esters
0.076g PABA methyl esters is weighed, in entering the 25mL reaction tubes equipped with magnetic stir bar, HCl is added
(0.13g) with the mixed liquor of DCE, 0.062g t-BuONO are added in reaction tube after reaction 5min, and is placed on ice salt bath
Middle stirring reaction 20min.0.3g support Buddhist nun reagent α are weighed again, and the acetonitrile copper of 0.314g tetrafluoro boric acids four, 0.034g sodium acid carbonates are incited somebody to action
They are sequentially added in reaction tube, the stirring reaction 10-20 hour at 50 DEG C, and after reaction terminates, reactant liquor is filtered successively, washed
And drying, then Jing column chromatography chromatogram separating-purifyings obtain colourless liquid 0.066g (yield is 65%).
Example nine, the synthesis of the 1- tert-butyl group -4- trifluoromethylbenzenes
0.075g 4- tert-butyl group aniline is weighed, in entering the 25mL reaction tubes equipped with magnetic stir bar, HCl (0.13g) is added
With the mixed liquor of DCE, 0.062g t-BuONO are added in reaction tube after reaction 5min, and it is anti-to be placed on stirring in ice salt bath
Answer 20min.Weigh again 0.3g support Buddhist nun reagent α, the acetonitrile copper of 0.314g tetrafluoro boric acids four, 0.034g sodium acid carbonates, by them successively
In adding reaction tube, the stirring reaction 10-20 hour at 50 DEG C, after reaction terminates, reactant liquor is filtered, washed and dried successively,
Again Jing column chromatography chromatograms separating-purifying obtains colourless liquid 0.084g (yield is 83%).
Example ten, 1- trifluoromethyl -4- fluorobenzene
Weigh 0.056g 4- fluoroanilines, in entering the 25mL reaction tubes equipped with magnetic stir bar, add HCl (0.13g) and
The mixed liquor of DCE, adds 0.062g t-BuONO in reaction tube after reaction 5min, and is placed on stirring reaction in ice salt bath
20min.0.3g support Buddhist nun reagent α are weighed again, and the acetonitrile copper of 0.314g tetrafluoro boric acids four, 0.034g sodium acid carbonates successively add them
In entering reaction tube, the stirring reaction 10-20 hour at 50 DEG C, after reaction terminates, reactant liquor is filtered, washed and dried successively, then
Jing column chromatography chromatogram separating-purifyings obtain colourless liquid 0.049g (yield is 60%).
Claims (9)
1. arylamine is converted into and all has extensively use in fields such as agricultural chemicals, medicine and organic materials by one kind under the conditions of better simply
The synthetic method of the trifluoromethyl aromatic compound on way, it comprises the following steps：
(1) with sodium metaperiodate, 2- iodo-benzoic acids, acetic anhydride, cesium fluoride and Ruppert reagents as Material synthesis support Buddhist nun reagent α；
(2) aromatic amine (1.0equiv) and hydrochloric acid (2.0equiv) are dissolved in DCE (5ml), stir 5-10min, low temperature bar
Part is lower to add nitrous acid special butyl ester (1.2equiv) reaction 30-60min, adds the acetonitrile copper of tetrafluoro boric acid four
(2.0equiv) Buddhist nun reagent α (3.0equiv) and sodium acid carbonate (0.8equiv), is held in the palm, mistake successively is reacted after terminating in low-grade fever reaction
Filter, wash and be dried, Jing column chromatography chromatograms obtain target product.
2. one kind as claimed in claim 1 is converted into arylamine in agricultural chemicals, medicine and organic material under the conditions of better simply
Deng the synthetic method of field all trifluoromethyl aromatic compounds with extensive use, its synthetic route is：
①
②
3. one kind as claimed in claim 1 is converted into arylamine in agricultural chemicals, medicine and organic material under the conditions of better simply
Deng the synthetic method of field all trifluoromethyl aromatic compounds with extensive use, it is characterized in that：Described in second step
Solvent is 1,2- dichloroethanes (DCE).
4. one kind as claimed in claim 1 is converted into arylamine in agricultural chemicals, medicine and organic material under the conditions of better simply
Deng the synthetic method of field all trifluoromethyl aromatic compounds with extensive use, it is characterized in that：Used by second step three
Fluoromethylation reagent is support Buddhist nun reagent α.
5. one kind as claimed in claim 1 is converted into arylamine in agricultural chemicals, medicine and organic material under the conditions of better simply
Deng the synthetic method of field all trifluoromethyl aromatic compounds with extensive use, it is characterized in that：The reaction temperature of second step
Spend for 40-80 DEG C.
6. one kind as claimed in claim 1 is converted into arylamine in agricultural chemicals, medicine and organic material under the conditions of better simply
Deng the synthetic method of field all trifluoromethyl aromatic compounds with extensive use, it is characterized in that：During the reaction of second step
Between be 10-20 hours.
7. one kind as claimed in claim 1 is converted into arylamine in agricultural chemicals, medicine and organic material under the conditions of better simply
Deng the synthetic method of field all trifluoromethyl aromatic compounds with extensive use, it is characterized in that：It is used in second step
Alkali is sodium acid carbonate.
8. one kind as claimed in claim 1 is converted into arylamine in agricultural chemicals, medicine and organic material under the conditions of better simply
Deng the synthetic method of field all trifluoromethyl aromatic compounds with extensive use, it is characterized in that：Arylamine, salt in second step
Sour nitrous acid special butyl ester, the acetonitrile copper of tetrafluoro boric acid four, support Buddhist nun's reagent α and sodium acid carbonate rate of charge are 1:2:1.2:2:3:0.8.
9. one kind as claimed in claim 1 is converted into arylamine in agricultural chemicals, medicine and organic material under the conditions of better simply
Deng the synthetic method of field all trifluoromethyl aromatic compounds with extensive use, it is characterized in that：In second step arylamine and
Dissolving with hydrochloric acid stirs 5-10min in DCE, and adds nitrous acid special butyl ester under cryogenic.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107827868A (en) * | 2017-11-14 | 2018-03-23 | 湖北工业大学 | The preparation method of 1 hydroxyl 1,2 benzenesulfonyl 3 (1H) ketone |
| WO2020246612A1 (en) * | 2019-06-07 | 2020-12-10 | ダイキン工業株式会社 | Fluorinated compound |
| CN115557823A (en) * | 2022-08-31 | 2023-01-03 | 浙江工业大学 | Method for synthesizing amide compound |
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| CN104710371A (en) * | 2013-12-13 | 2015-06-17 | 江南大学 | Preparation method of trifluoromethyl-containing benzo pyrazinamide |
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| CN104710371A (en) * | 2013-12-13 | 2015-06-17 | 江南大学 | Preparation method of trifluoromethyl-containing benzo pyrazinamide |
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| JIN XIE ET AL.: "Visible-Light-Promoted Radical C−H Trifluoromethylation of Free Anilines", 《ORGANIC LETTERS》 * |
| JULIE CHARPENTIER ET AL.: "Electrophilic Trifluoromethylation by Use of Hypervalent Iodine Reagents", 《CHEM. REV.》 * |
| KATARZYNA N. HOJCZYK ET AL.: "Trifluoromethoxylation of Arenes: Synthesis of ortho-Trifluoromethoxylated Aniline Derivatives by OCF3 Migration", 《ANGEWANDTE CHEMIE, INTERNATIONAL EDITION》 * |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107827868A (en) * | 2017-11-14 | 2018-03-23 | 湖北工业大学 | The preparation method of 1 hydroxyl 1,2 benzenesulfonyl 3 (1H) ketone |
| WO2020246612A1 (en) * | 2019-06-07 | 2020-12-10 | ダイキン工業株式会社 | Fluorinated compound |
| JPWO2020246612A1 (en) * | 2019-06-07 | 2020-12-10 | ||
| JP7373809B2 (en) | 2019-06-07 | 2023-11-06 | ダイキン工業株式会社 | fluoride compounds |
| CN115557823A (en) * | 2022-08-31 | 2023-01-03 | 浙江工业大学 | Method for synthesizing amide compound |
| CN115557823B (en) * | 2022-08-31 | 2023-12-05 | 浙江工业大学 | Method for synthesizing amide compounds |
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