Month: August 2021

These common heterocyclic compound, 452-66-4, name is 4-Chloro-1-fluoro-2-methylbenzene, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Product Details of 452-66-4

General procedure: Example 3Tandem Borylation/Dehalogenation of 1-Chloro-4-fluoro-3-Substituted- and 1-Bromo-4-fluoro-3-Substituted BenzenesTandem borylation/dehalogenation was also investigated as a strategy for the ortho-borylation of arenes that are substituted with an electron-withdrawing group. The scheme below illustrates the tandem borylation/dehalogenation methodology which was investigated. As discussed above, in the case of arenes that are substituted with an electron-withdrawing group, iridium-catalyzed C-H activation-borylation of the arene is typically governed by steric effects. In tandem borylation/dehalogenation, the substrate can include an electron-withdrawing group and a sacrificial atom (e.g., a halogen such as Cl or Br) positioned para to the electron-withdrawing group, so as to sterically hinder attack of the iridium catalyst at the otherwise sterically favored position meta to the electron-withdrawing group. As a result, iridium-catalyzed C-H activation-borylation of the arene exclusively generates the ortho-borylated (electronic) product. Subsequent dehalogenation can afford exclusively the desired electronic product.[0337] General Procedure for Borylation [0338] In a nitrogen atmosphere glovebox B2Pin2 (140 mg, 0.55 mmol) was weighed into a 20 mL vial containing a magnetic stir bar. [Ir(OMe)cod]2 (6.6 mg, 0.02 mmol) and 4,4?-di-tert-butyl-2,2?-dipyridyl ligand (5.4 mg, 0.02 mmol) were weighed into two separate test tubes, each being diluted with THF (2 mL). The [Ir(OMe)cod]2 solution was transferred into the 20 mL vial containing B2Pin2. This mixture was stirred until a golden yellow clear solution was obtained. The solution containing ligand was transferred into the vial, and the mixture was stirred until it became a dark brown color solution. The substrate (1 mmol) was added to the vial, which was then sealed. The reaction mixture stirred for 24 h at rt, after which the vial was removed from the glovebox. The reaction mixture was passed through a short plug of silica eluting with a 10:1 hexane/EtOAc solution (2×10 mL). The volatiles were removed by rotary evaporation affording the product, which was characterized using standard methodologies. 4-Chloro-1-fluoro-2-methylbenzene was borylated using the general procedure described above. After the workup, a white solid ( ) was obtained (0.173 g, 64%): mp 64-65 C.; 1H NMR (500 MHz, CDCl3) delta 7.49 (dd, J=3.0, 6.5 Hz, 1H), 7.22 (dd, J=2.0, 6.5 Hz, 1H), 2.23 (d, J=2.0 Hz, 3H), 1.34 (s, 12H); 13C NMR (125 MHz, CDCl3) delta 163.9 (d, J=247.5 Hz), 134.2 (d, J=5.7 Hz), 133.4 (d, J=8.5 Hz), 128.4 (d, J=2.9 Hz), 126.6 (d, J=21.9 Hz), 84.1, 24.7, 14.5 (d, J=3.9 Hz); 19F NMR (470 MHz, CDCl3) delta 109.9; 11B NMR (160 MHz, CDCl3) delta 29.8 (br s).

The synthetic route of 4-Chloro-1-fluoro-2-methylbenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Smith, III, Milton R.; Maleczka, JR., Robert E.; Li, Hao; Jayasundara, Chathurika; Oppenheimer, Jossian; Sabasovs, Dmitrijs; US2015/65743; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 104-77-8, name is 3-Chloro-N,N-diethylpropan-1-amine, molecular formula is C7H16ClN, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Recommanded Product: 104-77-8

Preparation 88 4-(Diethylamino)-1-(4-fluorophenyl)-1-butanone A suspension of 73.1 g (0.489 mol) 3-(diethylamino)-propyl chloride and 11.87 g (0.489 mol) of magnesium in 300 mL of tetrahydrofuran is initiated with 0.25 mL of 3M ethylmagnesium bromide in diethyl ether and is refluxed overnight. After this time, the reaction is allowed to cool to 40 C. and is treated with 29.6 g (0.245 mol) of 4-fluorobenzonitrile. The initial exotherm is followed by applied heat and the reaction is refluxed for 3 hr. After this time, the reaction is allowd to cool to room temperature and is quenched with 250 mL of water. This mixture is extracted with 2*250 mL of methylene chloride. The combined organic layers are acidifed to pH=1 with 2N aq. hydrochloric acid and the resulting layers separated. The aqueous extract is washed with 100 mL of methylene chloride and is made basic with 4N of sodium hydroxide. The aqueous mixture is extracted with 3*300 mL of methylene chloride. The combined organic layers are dried over sodium sulfate, filtered and the solvent distilled in vacuo to provide crude title compound. This liquid is distilled under vacuum to provide the title compound. NMR (CDCl3): delta=1.04(t,6), 1.92(m,2), 2.52(m,6), 3.20(t,2), 7.14(t,2) and 8.02 (m,2)ppm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 104-77-8, its application will become more common.

Reference:
Patent; Schering A.G.; US4851526; (1989); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 14862-52-3 as follows. Quality Control of 3,5-Dibromochlorobenzene

Under an argon atmosphere, 1,3-dibromo-5-chlorobenzene (2.70 g, 10.0 mmol) was dissolved in THF (38 mL). The mixture was cooled to -15 C., a THF solution (0.86 M, 12.3 mL, 10.5 mmol) of isopropyl magnesium chloride / lithium chloride complex was added, and the temperature was raised to 0 C. over 3 hours. Cyanuric chloride (5.53 g, 30.0 mmol) was added to the reaction mixture at the same temperature, then the temperature was raised to room temperature and stirred for 24 hours. Saturated ammonium chloride aqueous solution was added to the reaction mixture to stop the reaction, and then ethyl acetate was added. The organic layer was separated and the aqueous layer was extracted twice with ethyl acetate. The organic layers were combined, washed with water and dried over sodium sulfate.After filtering off the solid, the low-boiling fraction was removed under reduced pressure and the resulting residue was dried under vacuum to give crude product (6.74 g). The obtained crude product (6.6 g) was heated to 40 C. for 4 hours under reduced pressure (8 Pa), then heated to 50 C. and heated for 12 hours. After cooling to room temperature, purification by silica gel chromatography (eluent: hexane / ethyl acetate) gave the desired 2- (3-bromo-5-chlorophenyl) -4,6- dichloro-1,3,5- Triazine (82%, 2.80 g, 8.2 mmol).

According to the analysis of related databases, 14862-52-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TOSOH CORPORATION; SAGAMI CHEMICAL RESEARCH INSTITUTE; AIHARA, HIDENORI; SHONO, TOMOHIRO; (35 pag.)JP2017/160145; (2017); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 886762-39-6, The chemical industry reduces the impact on the environment during synthesis 886762-39-6, name is 3,4-Dichloro-2-fluoroaniline, I believe this compound will play a more active role in future production and life.

j00324j A solution of 3,4-dichloro-2-fluoroaniline (5.0 g, 31 mmol) and potassium 0-ethyl carbonodithioate (11 g, 67 mmol) in 1V N-dimethylformamide (50 mL) was stirred at 130 C for 16 hours. On completion, the reaction was cooled to room temperature, and hydrochloric acid (1M, 75 mL) was added. The mixture was stirred for 0.5 hour, resulting in formation of a solid. The solid was collected by filtration, washed with water (2 x 100 mL) and dried in vacuo to give compound B-26 (5.2 g, 79% yield) as a white solid. LCMS (B): tR=0.847 mi, (ES) m/z (M+H)237.0.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 3,4-Dichloro-2-fluoroaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FORUM PHARMACEUTICALS, INC.; ACHARYA, Raksha; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; COOK, Andrew, Simon; HARRISON, Bryce, Alden; McRINER, Andrew, J.; (267 pag.)WO2017/69980; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 2106-02-7, name is 2-Chloro-4-fluoroaniline, belongs to chlorides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 2106-02-7, Product Details of 2106-02-7

[000213] To a stirred solution of crude acid chloride (70 mg, crude) in CH2C12 (5 mL) under argon atmosphere were added 2-chloro-4-fluoroaniline 184 (25 mg, 0.17 mmol) and pyridine (0.07 mL, 0.86 mmol) at 0 C; warmed to RT and stirred for 16 h. The reaction was monitored by TLC; after completion of the reaction, the reaction mixture was diluted with water (20 mL) and extracted with CH2C12 (2 x 30 mL). The combined organic extracts were washed with 1 N HC1 (20 mL), 10% NaHCO3 solution (30 mL), brine (15 mL) dried over sodium sulfate, filtered and concentrated in vacuo to obtain crude. The precipitated material was either directly dried in vacuo or triturated or purified through silica gel column chromatography /preparative HPLC or by acid-base treatment to afford the desired compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-4-fluoroaniline, and friends who are interested can also refer to it.

Reference:
Patent; INDIANA UNIVERSITY RESEARCH AND TECHNOLOGY CORPORATION; ASSEMBLY BIOSCIENCES, INC.; TURNER, William W.; ARNOLD, Lee Daniel; MAAG, Hans; ZLOTNICK, Adam; WO2015/138895; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 4152-90-3, These common heterocyclic compound, 4152-90-3, name is (3-Chlorophenyl)methanamine, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: Compounds 5a?7a, 9a?11a, and 13a were synthetized using a microwave reactor with a focusedfield. Corresponding N-benzyl-3-chloropyrazine-2-carboxamide (0.6 mmol) was dissolved in methanol(3 mL) and appropriate benzylamine (1.8 mmol, 3 equiv.), along with pyridine (40 mg, 0.6 mmol,1 equiv.) as a base, were added. Our previous observations revealed that triethylamine (TEA) as a basecannot be used for microwave reactions. During the procedure, TEA is partially decomposed (probablyto diethylamine and similar species, which may act as undesired nucleophiles in the dehalogenationreaction). The use of pyridine as the base combined with benzylamines was experimentally verifiedin previous projects [18]. Conditions for synthesis were 150°C, 30 min, and 100 W. The progressof the reactions was monitored by TLC in system hexane/ethyl acetate 1:1. The reaction mixturewas adsorbed on silica by removing the solvents in vacuo and the product was purified by flashchromatography using gradient elution with ethyl acetate (0?100percent) in hexane. Products 7a and 10awere recrystallized from EtOH/H2O.

The synthetic route of 4152-90-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Semelkova, Lucia; Jand’ourek, Ond?ej; Kone?na, Klara; Paterova, Pavla; Navratilova, Lucie; Trejtnar, Franti?ek; Kubi?ek, Vladimir; Kune?, Ji?i; Dole?al, Martin; Zitko, Jan; McPhee, Derek J.; Molecules; vol. 22; 3; (2017);,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 62356-27-8, A common heterocyclic compound, 62356-27-8, name is 1-Bromo-3-chloro-2-methylbenzene, molecular formula is C7H6BrCl, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

EXAMPLE 175 6-(3-chloro-2-methylphenyl)-1,2-dihydro-2,2,4-trimethylquinoline (Compound 275, structure 4 of Scheme lI, where R1 =3-chloro-2-methylphenyl) This compound was prepared according to General Method 2 (EXAMPLE 9) from Compound 9 (70.0 mg, 0.22 mmol) and 2-bromo-6-chlorotoluene (45.2 mg, 0.22 mmol). The crude material was purified by flash column chromatography (75 ml silica, hexane to 5% ethyl acetate/hexane) to afford 63.1 mg (96%) of Compound 275. Data for Compound 275: 1 H NMR (400 MHz, acetone-d6) 7.30 (d, J=8.3, 1 H), 7.16 (m, 1 H), 6.95 (s, 1 H), 6.87 (d, J=10.2, 1 H), 6.54 (d, J=8.0, 1 H), 5.36 (s, 1 H), 5.25 (s, 1 H), 2.03 (s, 3 H), 1.28 (s, 6 H).

The synthetic route of 62356-27-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ligand Pharmaceuticals Incorporated; US5696130; (1997); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 627-42-9, name is 2-Methoxyethyl chloride, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C3H7ClO

Compound 5 (4.1 mL, 44.7 mmol) was added to and mixed with a first mixture including isovanillin (4.0 g, 26.3 mmol), potassium carbonate (6.5 g, 47.3 mmol), and dimethylformamide (DMF, 30 mL) to obtain a second mixture. The second mixture was then stirred at a temperature ranging from 85 C. to 90 C. for 20 hours, cooled to room temperature, and filtered via Buechner funnel, and the residue was washed with EtOAc. The EtOAc filtrate was washed with a sodium hydroxide aqueous solution (2N), water, and brine, and then dried over MgSO4, and concentrated to obtain a yellow oil (5.3 g, 97% yield). The spectrum analysis for the yellow oil obtained by the above procedures is: 1H NMR (400 MHz, CDCl3), delta (ppm): 9.83 (s, 1H), 7.47-7.42 (m, 2H), 6.97-6.95 (d, J=8.2 Hz, 1H), 4.23-4.21 (m, 2H), 3.93 (s, 3H), 3.81-3.79 (m, 2H), 3.44 (s, 3H); 13C NMR (100.6 MHz, CDCl3), delta (ppm): 190.7, 154.9, 148.8, 129.9, 126.8, 110.8, 110.7, 70.6, 68.2, 59.0, 56.0; LRMS-EI+ (m/z): 211 ([M+H]+, 13), 210 ([M]+, 100), 152(67), 123(4), 95(3), 77 (5), 59 (67); HRMS-TOF-ES+ (m/z): [M+H]+ calculated for C11H15O4, 211.0970, found: 211.0971. The yellow oil obtained was confirmed to be Compound 6 (4-methoxy-3-(2-methoxyethoxy)benzaldehyde).

According to the analysis of related databases, 627-42-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; National Chiao Tung University; Chao, Jui-I; Chen, Chin-Piao; Liu, Kuang-Kai; (16 pag.)US10251886; (2019); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 57310-39-1, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 57310-39-1 name is 3-Bromo-4-chlorotoluene, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

In a reactor equipped with a reflux condenser, a mixture of 3-bromo-4-chlorotoluene (compound CM20a above, 30.82 g, 150 mmol), 2,5-dimethylphenylboronic acid (compound CM20b above, 24.75 g, 165 mmol), anhydrous potassium carbonate (124.39 g, 900 mmol), palladium(II) acetate (0.67 g, 6 mmol), tricyclohexylphosphine (1.68 g, 12 mmol), dimethylacetamide (commercially available dehydrated product, 600 ml) and pivalic acid (15.32 g and 150 mmol) was stirred for 10 hours under an argon gas atmosphere while heating in an oil bath set to 150 C. After diluting with toluene (500 ml), rinsing and liquid separation were carried out 3 times using ion-exchanged water. Next, there was repeated twice a procedure of adding active white clay (product of Wako Pure Chemical Industries, Ltd., 60 g) to the obtained oil layer, stirring the mixture for 2 hours, and then passing it through Celite and a silica gel pad to remove the insolubles. After removing the solvent from the obtained solution by concentration under reduced pressure, recrystallizing purification was carried out (with a mixed solvent of chloroform and ethanol), and the deposited crystals were filtered out and dried under reduced pressure to obtain the target CM20c (35.5 g) as a solid with a faint yellow-white appearance. Yield: 51%. The HPLC-area percent value of the obtained compound CM20c measured under analysis conditions 1 was 99.3% (UV254 nm)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Bromo-4-chlorotoluene, and friends who are interested can also refer to it.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMTIED; Cambridge Display Teclmology Limited; Sekine, Chizu; Mikami, Satoshi; Anryu, Makoto; Kakimoto, Hidenobu; Steudel, Annette Regine; Humphries, Martin John; Kamtekar, Kiran Timothy; Garcia, Elena Hojas; Heidenhain, Sophie; Pegington, Ruth; (144 pag.)US9929347; (2018); B2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 15205-15-9, name is 2-Chloro-6-fluorobenzylamine, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Safety of 2-Chloro-6-fluorobenzylamine

General procedure: The pyrrole-3-carbaldehyde 3a-d (0.5 mmol) and a series of primary amines (0.6 mmol) were dissolved in dichloromethane (8 mL), and the resulting mixture was stirred for 30 min. The reaction was cooled at 0 C, and then NaBH(AcO)3 (1.25 mmol) and AcOH (0.5 mmol) were carefully added. The resulting mixture was stirred at room temperature for 16 h. The reaction was quenched with NaOH (1.0 M, 20 mL) and the product was extracted with ethyl acetate (3×25 mL). The organic extract was dried over anhydrous Na2SO4, filtered and evaporated in vacuo. The crude product was purified on the silica gel to afford 4a-b, 5a-c, 6a-r as yellow oil. Samples were dissolved in dichloromethane, and hydrogen chloride in diethyl ether solution (2.0M, 0.5mL) was added dropwise. The solvent was removed under reduced pressure to obtain pure solids as nuclear magnetic samples.

The synthetic route of 2-Chloro-6-fluorobenzylamine has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Ting; Tang, Yunxiang; Yang, Yang; An, Qi; Sang, Zitai; Yang, Tao; Liu, Pingxian; Zhang, Tianyu; Deng, Yong; Luo, Youfu; Bioorganic and Medicinal Chemistry Letters; vol. 28; 11; (2018); p. 2084 – 2090;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics