CN104211590A - Preparation method of 2, 4-dichloro-fluorobenzoyl chloride - Google Patents
Preparation method of 2, 4-dichloro-fluorobenzoyl chloride Download PDFInfo
- Publication number
- CN104211590A CN104211590A CN201410470239.5A CN201410470239A CN104211590A CN 104211590 A CN104211590 A CN 104211590A CN 201410470239 A CN201410470239 A CN 201410470239A CN 104211590 A CN104211590 A CN 104211590A
- Authority
- CN
- China
- Prior art keywords
- preparation
- chloro
- bis
- dichloro
- fluorobenzoyl chloride
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
- C07C51/62—Preparation of carboxylic acid halides by reactions not involving the carboxylic acid halide group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
- C07C51/64—Separation; Purification; Stabilisation; Use of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a preparation method of 2, 4-dichloro-fluorobenzoyl chloride, belonging to the technical field of synthesis of fine chemical intermediates. The preparation method comprises the following steps: by using 2, 4-dichloro fluorbenzene and oxalyl chloride as raw materials, performing acylation under catalysis of AlCl3; carrying out a reaction at 20-30 DEG C for 1.5-2.5 hours; and after reaction is ended, directly distilling at reduced pressure to obtain 2, 4-dichloro-fluorobenzoyl chloride. The method has the advantages that used raw materials are low in price and easily available, the safety is high, the process route is simple and short, and post-treatment is very simple. By adjusting the use level of the catalyst and the process operation, a relatively single target product can be obtained, the content of byproducts is low, the conversion ratio of raw materials is high, and the yield is over 98%; therefore, the preparation method is suitable for industrial continuous production.
Description
Technical field
The invention belongs to fine-chemical intermediate synthesis technical field, be specifically related to a kind of containing fluoroquinolones pharmaceutical intermediate 2, the preparation method of the chloro-5-fluorobenzoyl chloride of 4-bis-.
Background technology
2, the chloro-5-fluorobenzoyl chloride of 4-bis-is mainly used in the preparation of containing fluoroquinolones medicine, as Ciprofloxacin, norfloxicin, Enrofloxacin, Difloxacin, temafloxacin, also for the preparation of antipsychotic specifics Triperidol, trifluperidol, penfluridol, simultaneously also for the evaluation of agricultural chemical insecticide and plastics, resin.Containing fluoroquinolones medicine is the complete synthesis anti-infectives of a class coming out for 1979, has has a broad antifungal spectrum, a feature such as efficient, toxic side effect is little, convenient drug administration, has a wide range of applications clinically.
Up to the present, more about preparing the report of the chloro-5-fluorobenzoic acid of 2,4-bis-both at home and abroad, the chloro-5-fluorobenzoyl chloride of 2,4-bis-adopts the chloro-5-fluorobenzoic acid of 2,4-bis-and SOCl mostly
2carrying out acyl chloride reaction preparation, is mainly to take 2,4 dichloro fluorobenzene as raw material in these methods:
1) 2,4 dichloro fluorobenzene makes the chloro-5-fluorobenzoyl chloride of 2,4-bis-through friedel-crafts acylation, oxidation, acylation reaction.A) 2,4 dichloro fluorobenzene is at AlCl
3under catalysis, obtain the chloro-5-fluoro acetophenone of 2,4-bis-with excess acetyl chloride, then through hypochlorite oxidation, SOCl
2chloride makes (DE3435392, Chinese Journal of Pharmaceuticals, 1991,22 (12), 551, Chinese microbiotic magazine, 2004,29 (9), 529); B) nitric acid substitutes clorox and carries out oxidizing reaction (ES2006976, Jining Medical College journal, 2000,23 (2), 21, colleges and universities' chemical engineering journal, 2005,19 (5), 708, chemical engineer, 2007,141 (6), 48); C) vitriol oil and hydrogen peroxide carry out oxidizing reaction (US5481032); D) chloroacetyl chloride substitutes Acetyl Chloride 98Min. and carries out friedel-crafts acylation (CN1091418, Liaoning chemical industry, 1993, (6), 37, organic silicon-fluorine information, 2005, (3), 41).When the separation of the method intermediate product, purification, need to carry out low temperature crystallization, centrifugal or high vacuum rectification, cause the problems such as complex operation, facility investment increase, production cost height, and aluminum chloride easily distils and condenses.
2) 2,4 dichloro fluorobenzene is at AlCl
3under catalysis, with CCl
4trichloromethyl is introduced in reaction, adds H
2sO
4hydrolysis obtains the chloro-5-fluorobenzoic acid of 2,4-bis-(EP431373, US5241111), then with SOCl
2chloride makes the chloro-5-fluorobenzoyl chloride of 2,4-bis-.The method the first step generates approximately 30% by product (FCl
2c
6h
2)
2cCl
2, cause product separation difficulty, poor product quality.
3) 2,4 dichloro fluorobenzene obtains the chloro-5-fluorobenzoic acid of 2,4-bis-(JP0126538, CN1031074) through nitrated, reduction, diazotization, cyaniding, hydrolysis, then with SOCl
2chloride makes the chloro-5-fluorobenzoyl chloride of 2,4-bis-.The method step is oversize and relative yield is not high, with iron, makes catalyzer, and the organism in iron mud is difficult to separation, and uses hypertoxic cuprous cyanide or sodium cyanide.
4) 2,4 dichloro fluorobenzene obtains the chloro-5-fluorobenzoic acid of 2,4-bis-(EP431373, EP433124) through bromination, cyaniding, hydrolysis, then with SOCl
2chloride makes the chloro-5-fluorobenzoyl chloride of 2,4-bis-.In the method, bromination yield only has 70%, and uses hypertoxic cuprous cyanide or sodium cyanide, is difficult to realize industrialization.
5) 2,4 dichloro fluorobenzene is at AlCl
3under catalysis, direct and phosgene carries out acylation reaction and makes the chloro-5-fluorobenzoyl chloride of 2,4-bis-(JP01226859).In the method, have 5% by product (FCl
2c
6h
2)
2cO generates, and phosgene severe toxicity, and production security is poor.Use solid phosgene instead and substitute phosgene (Chemical Industry in Guangzhou, 2013,41 (15), 101), avoided by product (FCl
2c
6h
2)
2the generation of CO, but need low temperature crystallization, complex operation.
6) take 2,4-DCT as raw material, through nitrated, diazotization, fluoridize and obtain 2,4-Dichloro-5-fluorotoluene, chloro is introduced trichloromethyl, H
2sO
4hydrolysis obtains the chloro-5-fluorobenzoic acid of 2,4-bis-(DE3033157, DE3142856, Chinese Journal of Pharmaceuticals, 1996,27 (2), 83), then with SOCl
2chloride makes the chloro-5-fluorobenzoyl chloride of 2,4-bis-.The raw material of the method is easy to get, but operational path is long, fluoro diazonium salt excess Temperature, overall yield of reaction are lower.
The above-mentioned technique of DESCRIPTION OF THE PRIOR ART all has weak point, have that operational path is long, aftertreatment is loaded down with trivial details, equipment requirements is high, the use of severe poisonous chemicals, to environment and operator injure greatly, the problem such as yield is low, of poor quality, be not suitable for suitability for industrialized production.
Summary of the invention
For the above-mentioned problems in the prior art, starting material are cheap and easy to get, operational path is brief, production security is good, aftertreatment is simple, yield is high, quality is good to the object of the present invention is to provide one, be applicable to industrialization quantity-produced 2, the preparation method of the chloro-5-fluorobenzoyl chloride of 4-bis-, its solves, and in prior art, operational path is long, aftertreatment is loaded down with trivial details, equipment requirements is high, the use of severe poisonous chemicals, to environment and operator injure greatly, yield is low, of poor quality etc. is not suitable for the problem of suitability for industrialized production.
Described a kind of 2, the preparation method of the chloro-5-fluorobenzoyl chloride of 4-bis-, is characterized in that preparation method is as follows: in temperature, be at 0 ~ 30 ℃, to oxalyl chloride and AlCl
3mixture in drip 2,4 dichloro fluorobenzene, time for adding is 0.5 ~ 1 hour, after dropwising, keeping temperature is 20 ~ 30 ℃ of reactions 1.5 ~ 2.5 hours, underpressure distillation obtains the chloro-5-fluorobenzoyl chloride of 2,4-bis-, its reaction equation is as follows:
。
Described a kind of 2, the preparation method of the chloro-5-fluorobenzoyl chloride of 4-bis-, is characterized in that described 2,4 dichloro fluorobenzene and AlCl
3molar ratio be 1:0.1 ~ 0.5.
Described a kind of 2, the preparation method of the chloro-5-fluorobenzoyl chloride of 4-bis-, is characterized in that described 2,4 dichloro fluorobenzene and the molar ratio of oxalyl chloride are 1:0.5 ~ 0.55.
Described a kind of 2, the preparation method of the chloro-5-fluorobenzoyl chloride of 4-bis-, the time for adding that it is characterized in that dripping 2,4 dichloro fluorobenzene is 40-50min.
Described a kind of 2, the preparation method of the chloro-5-fluorobenzoyl chloride of 4-bis-, the dropping temperature that it is characterized in that dripping 2,4 dichloro fluorobenzene is 18 ~ 25 ℃.
Described a kind of 2, the preparation method of the chloro-5-fluorobenzoyl chloride of 4-bis-, is characterized in that holding temperature is 25 ℃, reacts 2 hours.
By adopting above-mentioned technology, compared with prior art, beneficial effect of the present invention is as follows:
1) to take oxalyl chloride and 2,4 dichloro fluorobenzene be raw material in the present invention, and above-mentioned raw materials is cheap and easy to get, toxicity is low, avoided severe poisonous chemicals use, solved environment and operator injured to the problems such as large;
2) the present invention uses aluminum chloride as catalyzer, and the consumption that defines this catalyzer and 2,4 dichloro fluorobenzene processing condition when, makes the target product that obtains single, and by-products content is few, and aftertreatment is very simple, and directly underpressure distillation can obtain, its AlCl
3consumption is few, and the AlCl reclaiming
3can directly apply mechanically 4-5 and criticize, yield, content are had no significant effect, save production cost, also greatly reduce the discharge of " three wastes ";
3) operational path of the present invention is brief, avoided that in existing technique, operational path is long, aftertreatment is loaded down with trivial details, equipment requirements is high, the use of severe poisonous chemicals, environment and operator have been injured to the problems such as large, and its feed stock conversion is high, yield is up to more than 98%, and applicable industrialization is produced continuously.
Embodiment
Below in conjunction with concrete case study on implementation, the present invention is further described.Be construed as; the preparation method of the invention process case is only for the present invention is described, rather than limitation of the present invention, and protection scope of the present invention is not limited in this; under design prerequisite of the present invention, preparation method's of the present invention simple modifications is all belonged to the scope of protection of present invention.
Embodiment 1
By oxalyl chloride (25.4g, 0.2mol), AlCl
3(16g, 0.12mol) add in reaction flask, control 25 ℃ of temperature, drip 2,4-dichlor fluorbenzene (66g, 0.4mol), in 30 minutes minutes, drip off, dropwise, continue to keep 25 ℃ of reactions 2 hours, the cut 89.6g of 143-144 ℃/35mmHg, pale yellow oily liquid body, yield 98.5% are collected in decompression.
In the present embodiment, in distillation residue, add oxalyl chloride, controlling temperature is 0 ~ 30 ℃, in 0.5 ~ 1 hour, drips 2,4-dichlor fluorbenzene, dropwises, and keeping temperature is 20 ~ 30 ℃ of reactions 1.5 ~ 2.5 hours, apply mechanically continuously 4 batches, all can obtain above-mentioned technique effect, illustrate that catalyzer can repeat cover.
Embodiment 2
By oxalyl chloride (28g, 0.22mol), AlCl
3(5.3g, 0.04mol) adds in reaction flask, controls 20 ℃ of temperature, within 60 minutes, drips 2,4 dichloro fluorobenzene (66g, 0.4mol), dropwises, and continues to keep 20 ℃ of reactions 2.5 hours, and the cut 89.4g of 143-144 ℃/35mmHg, yield 98.3% are collected in decompression.
Embodiment 3
By oxalyl chloride (25.4g, 0.2mol), AlCl
3(5.3g, 0.04mol) adds in reaction flask, controls 10 ℃ of temperature, within 40 minutes, drips 2,4 dichloro fluorobenzene (66g, 0.4mol), dropwises, and continues to keep 25 ℃ of reactions 2.5 hours, and the cut 84.5g of 143-144 ℃/35mmHg, yield 92.9% are collected in decompression.
Embodiment 4
By oxalyl chloride (25.4g, 0.2mol), AlCl
3(10.7g, 0.08mol) adds in reaction flask, controls 0 ℃ of temperature, within 30 minutes, drips 2,4 dichloro fluorobenzene (66g, 0.4mol), dropwises, and continues to keep 25 ℃ of reactions 2 hours, and the cut 89.2g of 143-144 ℃/35mmHg, yield 98.0% are collected in decompression.
Embodiment 5
By oxalyl chloride (25.4g, 0.2mol), AlCl
3(26.7g, 0.2mol) adds in reaction flask, controls 30 ℃ of temperature, within 60 minutes, drips 2,4 dichloro fluorobenzene (66g, 0.4mol), dropwises, and continues to keep 20 ℃ of reactions 1.5 hours, and the cut 61.3g of 143-144 ℃/35mmHg, yield 67.4% are collected in decompression.
Embodiment 6
By oxalyl chloride (25.4g, 0.2mol), AlCl
3(16g, 0.12mol) adds in reaction flask, controls 0 ~ 5 ℃ of temperature, within 30 minutes, drips 2,4 dichloro fluorobenzene (66g, 0.4mol), dropwises, and continues to keep 25 ℃ of reactions 2.5 hours, and the cut 89.4g of 143-144 ℃/35mmHg, yield 98.3% are collected in decompression.
Embodiment 7
By oxalyl chloride (25.4g, 0.2mol), AlCl
3(16g, 0.12mol) adds in reaction flask, controls 25 ~ 30 ℃ of temperature, within 1 hour, drips 2,4 dichloro fluorobenzene (66g, 0.4mol), dropwises, and continues to keep 30 ℃ of reactions 1 hour, and the cut 89.5g of 143-144 ℃/35mmHg, yield 98.4% are collected in decompression.
Embodiment 8
By oxalyl chloride (25.4g, 0.2mol), AlCl
3(16g, 0.12mol) adds in reaction flask, controls 18 ~ 22 ℃ of temperature, within 1 hour, drips 2,4-dichlor fluorbenzene (66g, 0.4mol), dropwises, continue to keep 20 ℃ of reactions 2.5 hours, the cut 89.3g of 143-144 ℃/35mmHg, yield 98.1% are collected in decompression.
Claims (6)
1. one kind 2, the preparation method of the chloro-5-fluorobenzoyl chloride of 4-bis-, is characterized in that preparation method is as follows: in temperature, be at 0 ~ 30 ℃, to oxalyl chloride and AlCl
3mixture in drip 2,4 dichloro fluorobenzene, time for adding is 0.5 ~ 1 hour, after dropwising, keeping temperature is 20 ~ 30 ℃ of reactions 1.5 ~ 2.5 hours, underpressure distillation obtains the chloro-5-fluorobenzoyl chloride of 2,4-bis-, its reaction equation is as follows:
。
2. as claimed in claim 1 a kind of 2, the preparation method of the chloro-5-fluorobenzoyl chloride of 4-bis-, is characterized in that described 2,4 dichloro fluorobenzene and AlCl
3molar ratio be 1:0.1 ~ 0.5.
3. as claimed in claim 1 a kind of 2, the preparation method of the chloro-5-fluorobenzoyl chloride of 4-bis-, is characterized in that described 2,4 dichloro fluorobenzene and the molar ratio of oxalyl chloride are 1:0.5 ~ 0.55.
4. as claimed in claim 1 a kind of 2, the preparation method of the chloro-5-fluorobenzoyl chloride of 4-bis-, the time for adding that it is characterized in that dripping 2,4 dichloro fluorobenzene is 40-50min.
5. as claimed in claim 1 a kind of 2, the preparation method of the chloro-5-fluorobenzoyl chloride of 4-bis-, the dropping temperature that it is characterized in that dripping 2,4 dichloro fluorobenzene is 18 ~ 25 ℃.
6. as claimed in claim 1 a kind of 2, the preparation method of the chloro-5-fluorobenzoyl chloride of 4-bis-, is characterized in that holding temperature is 25 ℃, reacts 2 hours.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201410470239.5A CN104211590B (en) | 2014-09-16 | 2014-09-16 | The preparation method of the chloro-5-fluorobenzoyl chloride of a kind of 2,4-bis- |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201410470239.5A CN104211590B (en) | 2014-09-16 | 2014-09-16 | The preparation method of the chloro-5-fluorobenzoyl chloride of a kind of 2,4-bis- |
Publications (2)
Publication Number | Publication Date |
---|---|
CN104211590A true CN104211590A (en) | 2014-12-17 |
CN104211590B CN104211590B (en) | 2016-01-20 |
Family
ID=52093552
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201410470239.5A Active CN104211590B (en) | 2014-09-16 | 2014-09-16 | The preparation method of the chloro-5-fluorobenzoyl chloride of a kind of 2,4-bis- |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN104211590B (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105669435A (en) * | 2015-02-15 | 2016-06-15 | 浙江永太科技股份有限公司 | Method used for preparing 2,4-dichloro-5-fluorobenzoyl chloride |
CN106966894A (en) * | 2016-12-07 | 2017-07-21 | 浙江工业大学 | A kind of method that pipe type continuously produces the fluorobenzoyl chloride of 2,4 dichloro 5 |
CN115784856A (en) * | 2022-11-09 | 2023-03-14 | 江苏新瀚新材料股份有限公司 | Method for synthesizing 4,4' -dihalogenobenzophenone |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20020062043A1 (en) * | 2000-11-09 | 2002-05-23 | Lars Rodefeld | Process for preparing optionally substituted biphenylcarbonyl chlorides |
CN101033198A (en) * | 2007-02-14 | 2007-09-12 | 浙江工业大学 | Compound of N-substituted-2,4-dichloro-5-fluorobenzamide, preparation and application thereof |
-
2014
- 2014-09-16 CN CN201410470239.5A patent/CN104211590B/en active Active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20020062043A1 (en) * | 2000-11-09 | 2002-05-23 | Lars Rodefeld | Process for preparing optionally substituted biphenylcarbonyl chlorides |
CN101033198A (en) * | 2007-02-14 | 2007-09-12 | 浙江工业大学 | Compound of N-substituted-2,4-dichloro-5-fluorobenzamide, preparation and application thereof |
Non-Patent Citations (3)
Title |
---|
CHRISTINE VALE&ACUTE RIO ET AL.: "Regioselective Chlorocarbonylation of Polybenzyl Cores and Functionalization Using Dendritic and Organometallic Nucleophiles", 《J. ORG. CHEM.》, vol. 65, no. 7, 16 March 2000 (2000-03-16), pages 1996 - 2002 * |
DOUGLASS F. TABER: "Unsymmetrical Diaryl Ketones from Arenes", 《J. ORG. CHEM.》, vol. 65, no. 1, 16 December 1999 (1999-12-16), pages 254 - 255, XP000877906, DOI: doi:10.1021/jo991055q * |
VERN G.DEVRIES ET AL.: "Potential Antiatherosclerotic Agents. 5. An Acyl-CoA:Cholesterol 0 -Acyltransferase Inhibitor with Hypocholesterolemic Activity", 《J. MED. CHEM.》, vol. 29, no. 7, 31 December 1986 (1986-12-31), pages 1131 - 1133 * |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105669435A (en) * | 2015-02-15 | 2016-06-15 | 浙江永太科技股份有限公司 | Method used for preparing 2,4-dichloro-5-fluorobenzoyl chloride |
CN105669435B (en) * | 2015-02-15 | 2017-12-08 | 浙江永太科技股份有限公司 | A kind of preparation method of the fluorobenzoyl chloride of 2,4 dichloro 5 |
CN106966894A (en) * | 2016-12-07 | 2017-07-21 | 浙江工业大学 | A kind of method that pipe type continuously produces the fluorobenzoyl chloride of 2,4 dichloro 5 |
CN106966894B (en) * | 2016-12-07 | 2019-10-18 | 浙江工业大学 | A kind of method of the pipe type continuously production chloro- 5- fluorobenzoyl chloride of 2,4- bis- |
CN115784856A (en) * | 2022-11-09 | 2023-03-14 | 江苏新瀚新材料股份有限公司 | Method for synthesizing 4,4' -dihalogenobenzophenone |
CN115784856B (en) * | 2022-11-09 | 2024-04-26 | 江苏新瀚新材料股份有限公司 | Method for synthesizing 4,4' -dihalogenated benzophenone |
Also Published As
Publication number | Publication date |
---|---|
CN104211590B (en) | 2016-01-20 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP3197454B1 (en) | Continuous flow carboxylation reaction | |
EP3700887B1 (en) | Processes for the preparation of aryl cycloalkylamine derivatives | |
KR20110031217A (en) | Process for the manufacture of alkenones | |
Wang et al. | A general method for synthesis of Se-trifluoromethyl esters through Iron-catalyzed trifluoromethylselenolation of acid chlorides | |
CN104211590B (en) | The preparation method of the chloro-5-fluorobenzoyl chloride of a kind of 2,4-bis- | |
Bigdeli et al. | Wet 2, 4, 6-trichloro [1, 3, 5] triazine (TCT) an efficient catalyst for synthesis of α, α′-bis (substituted-benzylidene) cycloalkanones under solvent-free conditions | |
CN107188840A (en) | A kind of synthetic method of asymmetric diaryl selenide compound | |
CN110066279A (en) | Perfluoroalkyl substituted indole and isoquinoline compound and preparation method thereof | |
CN104163775B (en) | A kind of production method of o-methyl-phenyl-azanol | |
JP2020183395A (en) | Process for the preparation of 1-(3,5-dichlorophenyl)-2,2,2-trifluoroethanone and derivatives thereof | |
Hu et al. | Henry reaction of fluorinated nitro compounds | |
Karabuga et al. | 3-Aminoquinazolinones as chiral ligands in catalytic enantioselective diethylzinc and phenylacetylene addition to aldehydes | |
CN102515999B (en) | Method for selectively oxidizing sulfide | |
Su et al. | Palladium-Catalyzed Three-Component 1, 4-Alkoxyarylation Reaction of [60] Fullerene | |
Raja et al. | Co (II) and 2-amino-perimidinium based new generation hybrid material promoted facile dimerization of aroyl chloride: A route to α-diketone | |
JP6176177B2 (en) | Method for oxidizing alcohols | |
CN109553524B (en) | Synthetic method of 2, 4-dichloro-5-fluorobenzoyl chloride | |
CN102584558A (en) | Preparation method of 1-(4-chlorphenyl)-2-cyclopropyl-1-acetone | |
CN102060679A (en) | Method for preparing aryl propanal derivatives | |
EP3207024B1 (en) | Process for the preparation of halo-substituted trifluoroacetophenones | |
CN108250086A (en) | The improvement synthetic method of one kind (R) -1- aryl -2- propylamine | |
CN102363614B (en) | Method for synthesizing 2-bromothiophene | |
Bhukta et al. | PIDA-Catalysed oxidative C–C bond cleavage for the direct synthesis of benzoic acids and antibacterial studies of the amides derivatives | |
CN109678652B (en) | Preparation method of ionic liquid promoted alpha, alpha-dichloroethyl cyclopropane | |
CN106810430B (en) | A kind of 2- Trifluoromethyl-1, the preparation method of 4- naphthoquinone derivatives |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant |