Month: August 2021

Adding a certain compound to certain chemical reactions, such as: 4863-91-6, name is 3-Chloro-5-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 4863-91-6, COA of Formula: C6H5ClFN

Example 1: Synthesis of N-(3-chloro-5-fluorophenyl)-4 nitrobenzo[c] [1,2,5] oxadiazol-5-amine Compound 1 [093] 5-Chloro-4-nitrobenzo[c][l,2,5]oxadiazole (1 15 mg, 0.58 mmol) was combined with 3-chloro-5-fluoroaniline (83.7 mg, 0.58 mmol) in DMF (0.55 mL), and the mixture was heated at 110C for 1.25 hours. The mixture was cooled to ambient temperature, resulting in the formation of a solid mass. This solid was resuspended in ethyl acetate and transferred to a larger volume of ethyl acetate (100 mL). This was sonicated to completely dissolve the solids. The organic layer was washed 5 times with water (50 mL) and brine, separated, and dried over Na2S04, then filtered and concentrated in vacuo. The resultant yellow solid was resuspended in ethyl acetate (3 mL), and filtered. The solids were washed with fresh ethyl acetate, and air-dried. N-(3-chloro-5-fluorophenyl)-4-nitrobenzo[c][l,2,5]oxadiazol-5-amine was obtained as a free-flowing yellow solid, (122 mg, 69%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Chloro-5-fluoroaniline, and friends who are interested can also refer to it.

Reference:
Patent; THE BOARD OF REGENTS OF THE UNIVERSITY OF TEXAS SYSTEM; BRUICK, Richard, K.; CALDWELL, Charles, G.; FRANTZ, Doug, E.; GARDNER, Kevin, H.; MACMILLAN, John, B.; SCHEUERMANN, Thomas, H.; TAMBAR, Uttam, K.; WO2014/78479; (2014); A2;,
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Some common heterocyclic compound, 13918-92-8, name is 2,4-Difluorobenzene-1-sulfonyl chloride, molecular formula is C6H3ClF2O2S, 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. Application In Synthesis of 2,4-Difluorobenzene-1-sulfonyl chloride

General procedure: To 5-(5-(5-Aminopyridin-3-yl)thiophen-2-yl)-2-methyl- isoindolin-1-one (49) (225 mg, 0.79 mmol) in dry pyridine (23 mL) under N2 at RT,was added dropwise, 2,4-difluorobenzenesulphonyl chloride (336 mg, 1.58 mmol) in CH2Cl2(3 mL) over 5 min. The suspension was heated to 45 C under N2 for 4 h., at which pointanother portion of 2,4-difluorobenzenesulphonyl chloride (169 mg, 0.79 mmol) in CH2Cl2 (2mL) was added. The whole mixture was left to stir for at 45 C under N2 for 16 h., then thesolvent removed under reduced pressure. The resulting residue was suspended in acetone (10mL), 1 M HCl (20 mL) added, and the entire mixture stirred for 10 minutes. The solid wasthen collected by filtration, washed well with 1 M HCl and water, dried, and purified bychromatography as described below. In cases where the bis-sulphonamide was also formed, a second step was introduced wherethe crude product above was treated with a 1:1 mixture of 1,4-dioxane and 2 M NaOH. Thecrude sulphonamide resulting from subsequent acidification of the reaction mixture wasisolated by filtration, washed well with water, and dried. Purification was carried out by flashcolumn chromatography (2% MeOH/CH2Cl2 as eluant), giving the title compound as a paleyellow solid (211 mg, 545).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 13918-92-8, its application will become more common.

Reference:
Article; Spicer, Julie A.; Miller, Christian K.; O’Connor, Patrick D.; Jose, Jiney; Huttunen, Kristiina M.; Jaiswal, Jagdish K.; Denny, William A.; Akhlaghi, Hedieh; Browne, Kylie A.; Trapani, Joseph A.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 4; (2017); p. 1050 – 1054;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 29671-92-9,Some common heterocyclic compound, 29671-92-9, name is Carbamimidic chloride hydrochloride, molecular formula is CH4Cl2N2, 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.

3.0 g of Arnold salt was added to 15 ml of methanol and 5 ml of water.Thereafter, 0.73 g of chloroformamidine hydrochloride and 0.53 g of sodium hydrogencarbonate were added thereto.The temperature was raised to 50 C to react. After 6 h of reaction, water was added to the system, and ethyl acetate was extracted.The opposite of water,The combined organic layers were washed with water, dried over anhydrous sodium sulfate and evaporatedThe yield was 83%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Carbamimidic chloride hydrochloride, its application will become more common.

Reference:
Patent; Anhui Haofan Biological Co., Ltd.; Lu Xuegen; Zhang Haiyan; Li Honglin; (6 pag.)CN109928933; (2019); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 203302-92-5, A common heterocyclic compound, 203302-92-5, name is 3-Bromo-2-chloro-6-fluorotoluene, molecular formula is C7H5BrClF, 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.

11. Reactions which are covered by Scheme 11; Example 11.1 : Preparation of (3-bromo-2-chloro-6-fluoro-phenyl)-acetic acid; Step 1; 3-Bromo-2-chloro-6-fluoro-toluene (8.0 g), N-bromosuccinimide (NBS) (6.42 g) and a catalytic amount of benzoyl peroxide in carbon tetrachloride (40 ml) were heated to reflux. A 500 watt tungsten halogen lamp was used to initiate the reaction. The reaction mixture was heated to reflux and irradiated for 30 minutes. The reaction mixture was allowed to cool and then filtered. The filtrate was concentrated to give a colourless oil which solidified on standing to give l-bromo-3-bromornethyl-2-chloro-4-fluorobenzene as an off-white solid (10.7 g). 1H NMR (CDCl3): 4.64 (d, 2H), 6.94 (t, IH), 7.58 (dd, IH) ppm.

The synthetic route of 203302-92-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SYNGENTA LIMITED; WO2008/9908; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 3972-56-3, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 3972-56-3, name is 1-tert-Butyl-4-chlorobenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Rh(ttp)Cl (1a) (10.0 mg, 0.012 mmol) and KOH (7.0 mg,0.125 mmol) were added in 4-chloro-tert-butylbenzene (2d)(1.0 mL). The red mixture was degassed for three freeze-thawpumpcycles, purged with N2 and heated at 150 C under N2 for 1day. Excess 4-chloro-tert-butylbenzene was removed by vacuumdistillation. The red residue was purified by column chromatographyon silica gel eluting with a solvent mixture of hexane/CH2Cl2(1:1). Red solid Rh(ttp) (4-tert-butylphenyl) (3d) [11] (9.2 mg,0.010 mmol, 85percent) was collected. Rh(ttp) (4-tert-butylphenyl) (3d)1H NMR (CDCl3, 400 MHz) d 0.23 (d, 2H, J 8.5 Hz), 0.35 (s, 9H),2.70 (s, 12H), 4.80 (d, 2H, J 8.8 Hz), 7.53 (t, 8H, J 6.4 Hz), 8.03 (d,4H, J 7.2 Hz), 8.08 (d, 4H, J 7.5 Hz), 8.78 (s, 8H).

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, 1-tert-Butyl-4-chlorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Qian, Ying Ying; Lee, Man Ho; Yang, Wu; Chan, Kin Shing; Journal of Organometallic Chemistry; vol. 791; (2015); p. 82 – 89;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 10061-02-6, 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 10061-02-6 as follows.

EXAMPLE 1; 382 g (406 ml) of DMF were initially charged in a Schmizzo and 137 g (141 ml) of 1.0 eq. NaOMe (30% solution in methanol) were added. This mixture was then heated to 60 C. (+/-3 C.) and 131 g (0.753 mol) of dimethyl isopropylmalonate were metered in within one hour. Subsequently, a methanol/DMF mixture (201 g) was distilled off under pressure (300 mbar to 60 mbar) and a temperature of 60 C.Thereafter, at 80 C. (+/-3 C.), 86 g (79 ml, 0.779 mol, 1.03 eq.) of 1,3-dichloropropene were metered in within one hour and the reaction mixture was then heated at 80 C. (+/-3 C.) for two hours. The reaction mixture was heated to 140 C. and a 25% solution of LiCl (0.6 eq.) in methanol (19 g of LiCl in 58 g of methanol) was metered in within two hours, and the reaction mixture was heated at 140-142 C. for a further 6 hours, in the course of which a portion of the methanol was distilled off and approx. 1.5 mol of gas (mainly CH3Cl and CO2) formed. The maximum amount of gas in the first half hour was approx. 6 liters. On completion of reaction, the solvent (DMF) and the excess methanol were distilled off substantially fully under reduced pressure. The remainder was admixed with 200 g of water, 89 g of 34% HCl and 200 g of MTBE, and the phases were separated. The organic phase was washed lx with 50 g of water and the solvent was removed under reduced pressure. Approx. 140 g of product were obtained, of which approx. 125 g were ester and 13 g the corresponding acid.

According to the analysis of related databases, 10061-02-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DSM Fine Chemicals Austria NFG GMBH & Co KG; US2008/207943; (2008); A1;,
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 39885-50-2 as follows. Quality Control of 2-Chloro-4-(trifluoromethyl)aniline

EXAMPLE 59 8-Chloro-N-((4-chlorophenyl)methyl)-4-hydroxy-5-trifluoromethyl-3-quinolinecarboxamide [] A mixture of 2-chloro-5-trifluoromethylaniline (3.91 g) and diethyl ethoxymethylenemalonate (4.0 mL) is heated at 190°C for 2 h and is then diluted with diphenyl ether (30 mL). The mixture is allowed to cool to rt, filtered, and the white solid is washed with hexane (2 x 10 mL) to afford 1.632 g of the diethyl aminomethylenemalonate. The resulting intermediate (2.63 g) is suspended in diphenyl ether (30 mL) and heated to reflux with a Dean-Stark trap for 3 h. The mixture is allowed to cool to rt and is then poured into hexane (50 mL). The solid is filtered and then washed with hexane (20 mL) and hexane/diethyl ether (1/1, 20 mL) to afford 1.273 g of the quinolinecarboxylate ethyl ester. The ester (400 mg) and 4-chlorobenzylamine (1.52 mL) are heated at 190 °C for 1 h. The resulting mixture is diluted with toluene (4 mL), allowed to cool to rt, and then poured into hexane (50 mL). The solvent is decanted and the remaining oil is crystallized (acetic acid, water) to afford 285 mg of the title compound as a brown solid. Physical characteristics are as follows: Mp 270-1 °C.1H NMR (300 MHz, DMSO) delta 12.33, 10.06, 8.68, 8.10, 7.86, 7.36, 4.52.13C NMR (100 MHz, DMSO) delta 175.05, 164.07, 144.36, 139.12, 138.20, 132.42, 131.85, 129.84, 128.77, 128.44, 126.70 (q), 125.84, 125.20, 122.22, 113.75, 42.00.IR (mull) 3187, 3091, 2925, 2855, 1657, 1604, 1567, 1531, 1462, 1417, 1377, 1366, 1348, 1307, 1272, 1210, 1158, 1139, 1128, 1106, 854, 841, 802, 726 cm-1.Anal. Found: C, 52.12; H, 2.78; N, 6.70; Cl, 16.85.MS (ESI-) for C18H11Cl2F3N2O2m/z 412 (M-H)-.

According to the analysis of related databases, 39885-50-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pharmacia & Upjohn Company LLC; EP1042295; (2005); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 14752-66-0, A common heterocyclic compound, 14752-66-0, name is Sodium 4-chlorobenzenesulfinate, molecular formula is C6H4ClNaO2S, 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: In a typical experiment, 1,3-dicarbonyl compounds (1 mmol), sodium sulfinates (1.2 mmol), DMSO (8 mL) and NH4I (4 mmol) were added to the undivided cell. The electrosynthesis was carried out in the undivided cell fitted with a Ni sheet cathode (2 cmx2.5 cmx0.02 cm) and a graphite rod anode at a constantcurrent (50 mA) at room temperature under magnetic stirring for 2 h and then continuously stirring for 5 h. After the reaction was finished, the electrolyte solution was decolorized with Na2S2O3, and then washed with distilled water (50 mL) and extracted withethyl acetate (10 mLx3). The solvent was removed under reduced pressure, and the crude product was purified by column chromatography on silica gel using petroleum ether-ethyl acetate (5:1) as eluent.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Pan, Xiao-Jun; Gao, Jian; Yuan, Gao-Qing; Tetrahedron; vol. 71; 34; (2015); p. 5525 – 5530;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 27139-97-5, name is 2-Bromo-4-chloro-1-methylbenzene, A new synthetic method of this compound is introduced below., category: chlorides-buliding-blocks

(b) into a 500mL three-neck bottle add 50g of compound 3, 50g of NBS (i.e. N-bromosuccinimide), 0.3g of BetaRho0 (i.e. dibenzoyl peroxide) and 300mL of carbon tetrachloride, the external temperature is raised at 90 C and the reaction is carried out for 24h (at this time, TLC showed complete reaction); pour the reaction solution into 500mL of ice water, adjust the pH at 10 with 2N (equivalent concentration) sodium hydroxide solution, layered extraction, combined organic phase, wash once with 5% sodium bicarbonate (mass concentration, the same below) solution, dry and then spin dry, separated by column chromatography and then obtained 52 g of compound 4 (yield is 75%)

The synthetic route of 27139-97-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Liu Ke; (11 pag.)CN108409659; (2018); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 19752-55-7, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 19752-55-7, name is 1-Bromo-3,5-dichlorobenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: 3,5-Dichloro-1-bromobenzene (7.46 g, 33.0 mmol) or 3,5-bis(trifluoromethyl)-1-bromobenzene (9.67 g, 33.0 mmol) was dissolved in ether (70 mL). To this solution, BuLi (1.58 M in hexane, 20.9 mL, 33.0 mmol) was added using syringe through septum cap at -78 °C for 20 min, and the mixture was stirred for 2 h at -78 °C. To the reaction mixture a solution of antimony (III) boromide (3.61 g, 10.0 mmol) in ether (50 mL) was added dropwise at -78 °C, and the resulting mixture was gradually raised to room temperature and stirred overnight. The reaction mixture was diluted with ether (150 mL) quenched with water. The mixture was extracted with ether (150 mL). The combined extracts were washed with brine and dried over anhydrous magnesium sulfate. The dried organic layer was concentrated under reduced pressure. The residue was purified on silica gel column chromatography to give 1n (hexane, 4.5 g, 80 percent yield) and 1o (hexane: CH2Cl2 4:1, 6.9 g, 91 percent yield).

The synthetic route of 1-Bromo-3,5-dichlorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yasuike, Shuji; Nakata, Kazuhide; Qin, Weiwei; Matsumura, Mio; Kakusawa, Naoki; Kurita, Jyoji; Journal of Organometallic Chemistry; vol. 788; (2015); p. 9 – 16;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics