Month: November 2020

A common heterocyclic compound, 6940-78-9, name is 1-Bromo-4-chlorobutane, molecular formula is C4H8BrCl, 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. 6940-78-9.

At 20 ~ 30 C, under stirring to N,N-dimethylformamide (1000 ml) was added 7-hydroxy-1H-quinolin-2-one (200.0 g) and potassium hydroxide (205.3 g, 1.2 eq), 240 ml of pure water was slowly added to the mixed solution at a controlled temperature of <40 C. The mixture was stirred at room temperature for about 15 minutes and 1-chloro-4-bromobutane (422 g, 2.0 eq) was added in one portion and then stirred at 40 C. for 5-6 h . The mixture was stirred for 1 h at room temperature and filtered. The cake was beaten by stirring in 1000 ml of water for 1 h, filtered, and the filter cake was refined in 10 times of methanol to obtain 240 g of the title compound (3) (yield: 77.0%). The synthetic route of 1-Bromo-4-chlorobutane has been constantly updated, and we look forward to future research findings. Reference:
Patent; Anhui Runsheng Pharmaceutical Co., Ltd.; Sun Mingzhe; Fang Cunjie; Zhao Dongsheng; Fang Congbin; Sun Yanbiao; Xu Kui; (4 pag.)CN106496206; (2017); A;,
Chloride – Wikipedia,
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6940-78-9, Adding some certain compound to certain chemical reactions, such as: 6940-78-9, name is 1-Bromo-4-chlorobutane, 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 6940-78-9.

Add p-nitrophenol (1.39g, 10mmol) and potassium carbonate (1.38g, 10mmol) to 25ml acetonitrile, then add dropwise1-Bromo-4-chlorobutane (1.7 ml, 15 mmol) was refluxed at 80 C overnight. After the reaction is completed, water is added to dissolve potassium carbonate, andExtract with ethyl acetate, wash the organic phase with saturated sodium bicarbonate and brine.Evaporation to dryness gave a white solid (1.98 g, yield 86%).The product was used directly in the next reaction without purification.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 6940-78-9.

Reference:
Patent; Beijing Xinchen Pharmaceutical Technology Co., Ltd.; Yin Yuxin; Zhai Zheng; (37 pag.)CN109593064; (2019); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 626-43-7, name is 3,5-Dichloroaniline, 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 626-43-7, 626-43-7

EXAMPLE 6; Preparation of 1,3,5-triaminobenzene from 3,5-dichloroaniline; hydrolysis with sulfuric acid of the 1,3,5-triaminobenzene to phloroglucinol, and purification; A pressurized vessel is charged with 30 g (18.6 mmol) of 3,5-dichloroaniline and 1.5 g of copper chloride in 160 ml of 28% aqueous ammonia. The mixture is heated at 190 C. and under a pressure of 37 bars for 24 hours. The contents of the vessel are poured into 200 ml of water and then the excess ammonia is removed. Then 37 g of 98% sulfuric acid are added and the mixture is heated at 110 C. for 20 hours. Following filtration, the solution is concentrated to a third and then cooled in an ice bath until the phloroglucinol precipitates. The precipitate obtained is subsequently recrystallized from 350 ml of a water-ethanol (93 V-7 V) mixture.

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, 3,5-Dichloroaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PHV ANALYITIC; US2005/165256; (2005); A1;,
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. 108-41-8, name is 1-Chloro-3-methylbenzene, This compound has unique chemical properties. The synthetic route is as follows., 108-41-8

General procedure: KBr (29.8 mg, 0.25 mmol, 1.0 equiv), 1-ethyl-4-nitrobenzene (1a) (41.6 mg, 0.275 mmol, 1.1 equiv), Oxone (153.9 mg, 0.25 mmol, 1.0 equiv), CH2Cl2 (0.25 mL) and H2O (180.0 mg, 0.18 mL, 40.0 equiv) were added, in accordance with the order, to a 15-mL oven-driedtube. The reaction tube was equipped with a magnetic stir bar and sealed with a Teflon-lined cap at once after the addition of the H2O. Then, the tube was placed on a magnetic stirrer (speed 300 rpm) and irradiated with a 0.5 W LED at a distance of 5 cm for 20 h at rt. After the reaction was finished, the reaction mixture was quenched with Na2SO3. Water (15 mL) was added and the mixture extracted with CH2Cl2 (3 ¡Á 5 mL). The organic phase was combined and dried with anhydrous Na2SO4. The solvent was evaporated under reduced pressure to give the crude product that was purified by flash column chromatography (petroleum ether/EtOAc mixtures). Compound 3a was obtained as a light yellow solid; yield: 53.6 mg (93%).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Zhao, Mengdi; Li, Meiqi; Lu, Wenjun; Synthesis; vol. 50; 24; (2018); p. 4933 – 4939;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 33863-76-2, name is 1-Bromo-3-chloro-5-fluorobenzene, 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. 33863-76-2

EXAMPLE 13-Chloro-5-{[5-chloro-l-(lH-pyrazolo[3,4-]pyridin-3-ylmethyl)-lH-indazol-4- yl] oxy } benzonitrileStep 1 : 3-Bromo-5-chlorophenyl 2-chloro-5-fluorophenyl ether; To a solution of 2-chloro-5-fluorophenol ( 82.3 g, 562 mmol) and l-bromo-3- chloro-5-fluorobenzene (124g, 590 mmol) in NMP (200 mL) was added potassium carbonate (155g, 1.123mol). The resulting mixture was then heated to 1400C and maintained at 14O0C for 30 hours, after which the mixture was poured into water (1500 mL) and extracted with EtOAc (2500 + 1500 mL). The combined extracts were washed with water and brine. This solution was concentrated on the rotary evaporator and the residue was distilled at high vacuum at 135-1900C to give the title compound as a clear, colorless liquid. leta NMR (CDCI3) delta 7.45 (dd, 1eta, J=9.0 and 4.5 hz), 7.28(dd, 1eta, J=I .7Hz), 7.26(s, IH), 7.00(dd, Ih, J=I .95Hz), 6.92(ddd, IH, J=10.5, 7.6 and 2.7Hz), 6.89(dd, IH, J=I.95Hz).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 33863-76-2.

Reference:
Patent; MERCK & CO., INC.; WO2008/76223; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

A common compound: 108-37-2, name is 1-Bromo-3-chlorobenzene, belongs to chlorides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 108-37-2

(Setting-Up and Reaction) To a 50 mL two-necked round-bottomed flask, [PdCl (pi-allyl) ]2 (10.8 mg, 0. 05 mol%) and cBRIDP (41.8 mg, 0.2 mol%) were added. A three-way stopcock was attached to the flask, and the inside was purged with nitrogen. Subsequently, anhydrous THF (5 mL) was added, and the mixture was shaken at room temperature for 1 minute and further diluted with anhydrous xylenes (20 mL) to prepare a catalyst solution (25 mL). On the other hand, to a 300 mL four-necked round-bottomed flask, a three-way stopcock, a Teflon-coated magnetic stirring bar, a condenser, a 50 mL dropping funnel, and a thermometer were attached, and the inside was purged with nitrogen. To this flask, carbazole (20.4 g, 178.8mmol, 1.03eq.), anhydrous xylenes (100 mL), and anhydrous THF (10 mL) were sequentially added, and the obtained reactant suspension was cooled to 5C by use of an ice-water bath. Subsequently, a MeMgCl/THF solution (3.02 mol/L, 40.0 mL, 120.8 mmol, 1.02 eq.) was placed in the dropping funnel, and added dropwise over 20 minutes, while the reactant suspension was being stirred, and the inside temperature was being kept at 20C or below. Then, the dropping funnel was rinsed with anhydrous xylenes (20 mL). Subsequently, 3-bromochlorobenzene (14.0 mL, 118.4 mmol, 1.0 eq.) and the catalyst solution (25 mL) were sequentially added to the reaction solution, and then the mixture was stirred for 1 hour under reflux (approximately 110C). Reaction Conversion: >99.9% (GC). (Post Treatment) After the obtained suspension had been cooled to room temperature, water (60 mL) and ammonium chloride (3.2 g, approximately 0.5 eq.) were added. The mixture was filtered by use of diatomaceous earth, the aqueous layer was separated (Aqueous Layer 1: pH=9), and further the organic layer was washed with water (60 mL) (Aqueous Layer 2: pH=7). The organic layer was concentrated under reduced pressure, and the obtained brown viscous liquid was purified by silica gel column chromatography (Eluent: n-hexane/toluene=4/1 to 2/1) to give 32.4 g of title compound (8) as a colorless viscous liquid. Isolated Yield: 98.5%. For exact measurement of the weight, a toluene solution of title compound (8) (25% by weight, 0.900 mmol/g) was prepared after the purification and used in the second step. 1H NMR (300 MHz, CDCl3): delta=8.13 (dt, J=7.5, 0.9 Hz, 2H), 7.58 (t, J=2.1 Hz, 1H), 7.56-7.38 (m, 8H), 7.35-7.25 (m, 2H). 13C NMR (75 MHz, CDCl3): delta=140.5, 140.0, 135.4, 130.8, 127.6, 127.2, 126.1, 125.2, 123.5, 120.4, 120.3, 109.6.

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, 108-37-2, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Takasago International Corporation; Nakayama, Yuji; Yokoyama, Naota; EP2937355; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 60811-18-9 name is 4-Bromo-1-chloro-2-fluorobenzene, 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. 60811-18-9

[Example 112] Preparation of 4-(trans-4-(2-(trans-4-n-propyl-4-silacyclohexyl)ethyl)cyclohexyl)-3′-fluoro-4′-cyanobiphenyl 20.9 g (0.1 mol) of 1-bromo-4-chloro-3-fluorobenzene was dripped into a mixture of 2.5 g (0.11 mol) of magnesium and 300 ml of THF to obtain a Grignard’s reagent. This solution was then dripped into a 500 ml THF solution of 0.5 g of tetrakis triphenylphosphine palladium and 43.6 g (0.1 mol) of 4-(trans-4-(2-(trans-4-n-propyl-4-silacyclohexyl)ethyl)cyclohexyl)phenyl bromide. After a conventional after treatment, purification was conducted by means of chromatography to obtain 36.4 g (yield 75.1%) of 4-(trans-4-(2-(trans-4-n-propyl-4-silacyclohexyl)ethyl)cyclohexyl)-3′-fluoro-4′-cyanobiphenyl was obtained.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-1-chloro-2-fluorobenzene, and friends who are interested can also refer to it.

Reference:
Patent; Shin-Etsu Chemical Co., Ltd.; US5582764; (1996); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

A common heterocyclic compound, 108-41-8, name is 1-Chloro-3-methylbenzene, molecular formula is C7H7Cl, 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. 108-41-8.

General procedure: Under an N2 atmosphere, KOtBu (1.3 mmol), complex 1 (1 mol %), dioxane (2 ml), amines (1.3 mmol) and aryl chlorides (1.0 mmol) were successively added into a Schlenk tube. The mixture was stirred vigorously at 90 C for 4 h. Then the solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel (eluent: PE/EA = 15:1) to give the pure products. The reported yields are the average of two runs.

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

Reference:
Article; Nirmala, Muthukumaran; Saranya, Gandhi; Viswanathamurthi, Periasamy; Bertani, Roberta; Sgarbossa, Paolo; Malecki, Jan Grzegorz; Journal of Organometallic Chemistry; vol. 831; (2017); p. 1 – 10;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

6940-78-9, 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. 6940-78-9 name is 1-Bromo-4-chlorobutane, 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.

1-bromo-4-chlorobutane (3.4 g, 20 mmol), anhydrous potassium carbonate powder (4.14 g, 30 mmol) and 7-hydroxy-3,4-dihydro-2(1H)quinolinone 10 mmol)Was added to 10 ml of acetone, refluxed for 24 hours,, the reaction solution was evaporated to dryness, and the mixture was partitioned with 20 ml portions of dichloromethane and water. The organic layer was extracted with 20 ml of water * 2 and 20 ml of saturated brine successively, dried over anhydrous magnesium sulfate , Evaporate to dryness to give a pale yellow powder. The obtained powder is washed with slurry with 20 ml * 3 of n-hexane, filtered, and dried to obtain 1.98 g of 7-(4-chlorobutoxy)-3,4-dihydro-2(1H)quinolinone. Yield is 78%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-4-chlorobutane, and friends who are interested can also refer to it.

Reference:
Patent; JIANGSU HENGYI PHARMACEUTICAL COMPANY LIMITED; SHANGHAI INSTITUTE OF PHARMACEUTICAL INDUSTRY; Li, JIANQI; PENG, SHAOPING; CAI, WANGPING; GAO, KAI; (39 pag.)JP5714152; (2015); B2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

A common heterocyclic compound, 1996-30-1, name is 3-Bromo-4-fluorochlorobenzene, molecular formula is C6H3BrClF, 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. 1996-30-1.

[0136] A solution of 2-bromo-4-chloro-1-fluorobenzene (175 muL, 1.377 mmol) in THF (4.59 mL) at 78 C. was treated with n-BuLi (2.6 M, 741 muL, 1.928 mmol) and the reaction mixture was stirred for 30 min. To this was added tert-butyl 4-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate (250 mg, 0.918 mmol) in one portion. The cooling bath was removed and the resulting reaction mixture was allowed to warm to rt and stirred for 1.5 h. Purification by automated flash silica gel chromatography using 10% EtOAc in hexanes afforded tert-butyl 4-(5-chloro-2-fluorobenzoyl)piperidine-1-carboxylate (287.9 mg, 92%) as a yellow oil. ESI-MS m/z [M+Na]+ 364.20

The synthetic route of 3-Bromo-4-fluorochlorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; Brown, Jason; Hitchcock, Steve; Hopkins, Maria; Kikuchi, Shota; Monenschein, Holger; Reichard, Holly; Schleicher, Kristin; Sun, Huikai; Macklin, Todd; US2015/175602; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics