Month: October 2020

96558-78-0, A common heterocyclic compound, 96558-78-0, name is 3-Bromo-5-chlorophenylamine, molecular formula is C6H5BrClN, 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.

To a solution of compound A (1 g, 4.8 mmol, 1 eq ), compound B (1.2 g, 7.3 mmol, 1.5 eq ) and K2CO3 (2.0 g, 14.5 mmol, 3 eq) in 5 mL of dioxane and 1 mL of H2O was added Pd(dppf)Cl2 (354.4 mg, 484.3 pmol, 0.1 eq) under N2. The mixture was stirred at 100C for 12 hours. Then it was partitioned between 30 mL of water and 60 mL of ethyl acetate. The organic phase was separated, washed with 30 mL of brine, dried over Na2SC>4, filtered and concentrated under reduced pressure to give the crude product, which was purified by column chromatography (S1O2, eluting with a gradient of petroleum ether: ethyl acetate = 1 :0 to 1 : 1) to give 440 mg of compound C (2.6 mmol, 54.2% yield) as a brown oil.

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

Reference:
Patent; AQUINNAH PHARMACEUTICALS, INC.; VACCA, Joseph, P.; WAGER, Travis, T.; (383 pag.)WO2020/117877; (2020); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 13526-66-4, name is 3-Bromo-6-chloroimidazo[1,2-b]pyridazine, molecular formula is C6H3BrClN3, 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. 13526-66-4

13.9 g (59.8 mmol) 3-bromo-6-chloro-imidazo[l,2-b]pyridazine were suspended in 508 mL 1,4-dioxane. 10.1 g (62.8 mmol) 2-benzofuranylboronic acid, 2.76 g (2.29 mmol) tetrakis(triphenylphosphino)palladium-(0) and 19.0 g (179 mmol) sodium carbonate were added. The obtained mixture was heated to 100C for 24 h. 400 mL of a saturated aqueous ammonium chloride solution were added. The obtained mixture was extracted with ethyl acetate. The combined organic layers were washed with brine and dried over magnesium sulfate. After evaporation of the solvent, the obtained solid material was digested in 40 mL of a mixture of dichloromethane and methanol (8:2), filtered off and dried in vacuo to yield 5.42 g (44%) of the title compound as solid material. ^-NMR (300M HZ, DMSO-d6): delta [ppm] = 7.23 – 7.40 (2H), 7.51 (1H), 7.59 – 7.67 (2H), 7.77 (1H ), 8.33 – 8.40 (2H).LCMS (Method 1) : Rt= 1.35 min; MS (ESIpos) m/z = 270 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 13526-66-4, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; EIS, Knut; PUeHLER, Florian; ZORN, Ludwig; SCHULZE, Volker; SUeLZLE, Detlev; LIENAU, Philip; WENGNER, Antje, Margret; PETERSEN, Kirstin; BOeMER, Ulf; WO2014/128093; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

112-26-5, 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. 112-26-5 name is 1,2-Bis(2-chloroethoxy)ethane, 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.

A suspension of4.5 g (14 mmol) of 2-diphenylphosphorylmethylphenol[12] and 0.56 g (14 mmol) of finely divided NaOHin 35 mL of dry dioxane was stirred for 0.5 h at 95C,next 1.3 g (7 mmol) of 1,8-dichloro-3,6-dioxaoctanewas added, the mixture was refluxed for 8 h, concentratedunder reduced pressure, 50 mL of water wasadded to the residue, the mixture was acidified withconcentrated HCl to pH 1 and extracted with CHCl3(3 ¡Á 25 mL). The extract was washed with diluted (1 : 2)HCl (2 ¡Á 30 mL), water (2 ¡Á 30 mL), and concentratedunder reduced pressure. The residue was dissolvedin 40 mL of anhydrous acetonitrile, 2.25 g (15 mmol) ofdry NaI was added, the mixture was refluxed for 1 h,cooled to 8C, the precipitate was separated by filtration,washed with boiling acetonitrile (10 mL) anddried in a vacuum. The precipitate was identified as a1 : 1 complex of L with NaI. Yield 4.3 g, 77%. ForC44H44INaO6P2 anal. calcd. (%): C, 60.01; H, 5.04; P,7.03. Found (%): C, 59.81, 59.73; H, 4.52, 4.90;P, 6.63, 6.91.

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; Bezhin; Dovhyi; Lyapunov, A. Yu.; Baulin; Baulin; Tsivadze, A. Yu.; Russian Journal of Inorganic Chemistry; vol. 64; 9; (2019); p. 1178 – 1185; Zh. Neorg. Khim.; vol. 64; 9; (2019); p. 997 – 1005,9;,
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. 344-19-4 name is 2,6-Dichloro-4-fluoroaniline, 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. 344-19-4

To a solution of 6.07 g (19.1 mmol) of ethyl 2-[(2,6-dichloropyridin-3-yl)carbonyl]-3-ethoxyacrylate (CAS 157373-27-8) and 4.81 g (26.7 mmol) of 2,6-dichloro-4-fluoroaniline in 30 ml DCM were added 23.3 ml (134 mmol) of DIPEA, and the mixture was stirred at RT for 4 h. Subsequently, 2.64 g (19.1 mmol) of potassium carbonate were added and the mixture was heated under reflux overnight. The mixture was diluted with 200 ml of DCM and washed twice with 75 ml of 1 M aqueous hydrochloric acid. The organic phase was dried over sodium sulphate and filtered, and the solvent was removed under reduced pressure. The suspension obtained was stirred with 40 ml of tert-butyl methyl ether, and the precipitate was filtered off with suction, washed with 10 ml of tert-butyl methyl ether and dried under high vacuum. 3.81 g (45% of theory, 94% purity) of the title compound were obtained. LC-MS (Method 1): Rt=1.04 min; MS (ESIpos) m/z 415 [M+H]+. 1H NMR (400 MHz, DMSO-d6): delta [ppm]=8.88 (s, 1H), 8.65 (d, 1H), 7.92 (d, 2H), 7.69 (d, 1H), 4.25 (q, 2H), 1.28 (t, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,6-Dichloro-4-fluoroaniline, and friends who are interested can also refer to it.

Reference:
Patent; Bayer Pharma Aktiengesellschaft; TELLER, Henrik; STRAUB, Alexander; BRECHMANN, Markus; MUeLLER, Thomas; MEININGHAUS, Mark; NOWAK-REPPEL, Katrin; TINEL, Hanna; MUeNTER, Klaus; FLIEGNER, Daniela; MONDRITZKI, Thomas; BOULTADAKIS ARAPINIS, Melissa; MARQUARDT, Tobias; VAKALOPOULOS, Alexandros; REBSTOCK, Anne-Sophie; WITTWER, Matthias Beat; (342 pag.)US2018/297994; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

328-84-7, 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. 328-84-7, name is 3,4-Dichlorobenzotrifluoride, This compound has unique chemical properties. The synthetic route is as follows.

(a) A mixture of 3,4-dichlorobenzotrifluoride (48 g), hydrazine hydrate (65 g) and pyridine (240 g) was stirred and heated at 150 C. for 6 hours in an autoclave at a pressure of 4 bar. The cooled mixture was quenched with sodium hydroxide solution and the organic layer evaporated in vacuo. The residue was dissolved in diethyl ether, washed (water) and the ether evaporated to give 2-chloro-4-trifluoromethylphenylhydrazine and 2-chloro-5-trifluoromethylphenylhydrazine as a 95/5 mixture (36 g),

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:
Patent; Aventis CropScience, S.A.; US6410737; (2002); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

1871-57-4, A common compound: 1871-57-4, name is 3-Chloro-2-chloromethyl-1-propene, 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.

[0102] A tubular reactor was configured 300 with a static mixer 305, a T-mixer 310 and an elevated temperature stage 322 as illustrated schematically in FIG. 8. An organic stream 328 containing 3-chloro-2-(chloromethyl)prop-1-ene (1 equiv.), CHBr3 (5 equiv.), 18-crown-6 (5 mol %), pinacol (8.5 mol %), and methylene chloride (4 vol.) was mixed with an aqueous33% NaOH stream 329 at about 70C using mixers 305, 310 in the tubular reactor 300 to form1,1 -dibromo-2,2-bis(chloromethyl)cyclopropane 330. Flow rates were controlled by using the back pressure regulator 370 and by using the syringe pumps 335, 340 to deliver the organic and aqueous streams. The mixers 335, 340 were located in the elevated temperature stage 322 as illustrated in FIG. 8 and included a T-junction (T-mixer) 310 and a 29 element in-line static mixer 305 having a diameter about the same as that of the reactor tubing. The static mixer 305 includes counterhelices to achieve mixing of the biphasic stream in laminar flow. The residence time in the elevated temperatures stage 322 was about one hour. The yield of 1,1 – dibromo-2,2-bis(chloromethyl)cyclopropane 330 was – 9%.

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-Chloro-2-chloromethyl-1-propene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ZENO ROYALTIES & MILESTONES, LLC; PINCHMAN, Joseph, Robert; BUNKER, Kevin, Duane; BIO, Matthew, M.; BREEN, Christopher; CLAUSEN, Andrew, M.; FANG, Yuanqing; LI, Hui; SHEERAN, Jillian, W.; (61 pag.)WO2019/51038; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

56961-77-4, These common heterocyclic compound, 56961-77-4, name is 1-Bromo-2,3-dichlorobenzene, 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.

1-bromo-2,3-dichlorobenzene (15.0 g, 66.4 mmol) and aniline (12.7 g, 136.1 mmol) were added to toluene in a three-necked flask. Dissolved in 450ml sodium tert-butoxide (9.6g, 99.6mmol), bis (tri-tert-butylphosphine) palladium (0) (0.7 g, 1.3 mmol) was added thereto, followed by stirring for 6 hours under reflux conditions under argon atmosphere. After the reaction was completed, the reaction mixture was cooled to room temperature, H 2 O was added thereto, and the reaction solution was transferred to a separatory funnel to extract. The extract was dried over MgSO 4, concentrated and the sample was purified by silica gel column chromatography to give 14.7 g of intermediate A-1. (Yield 75%)

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 56961-77-4.

Reference:
Patent; LG Chem, Ltd.; Seo Sang-deok; Park Tae-yun; Lee Dong-hun; (32 pag.)KR2019/141620; (2019); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

118-69-4, 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 118-69-4 as follows.

step one:2,6-dichlorotoluene (100 g, 0.62 mol) was added to 1000 ml of dichloromethane at room temperature, and aluminum trichloride (165.6 g, 0.68 mol) was added thereto, and the temperature was controlled below 30 C.Acetyl chloride (97.5 g, 1.24 mol) was added dropwise to the reaction system at a rate of 20 drops per minute.After the completion of the dropwise addition, the temperature was raised to 40 C and refluxed for 12 hours.After the completion of the reaction, the reaction system was cooled to room temperature, and the reaction mixture was poured into 1000 ml of ice water, extracted with dichloromethane (500 ml ¡Á 3), and the organic phase was combined, washed with saturated brine (600 ml ¡Á 2), anhydrous sulfuric acid Magnesium is filtered after drying,The filtrate was concentrated under reduced pressure to give a red brown oil.106 g, crude yield was 84.2%.

According to the analysis of related databases, 118-69-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SHANDONG BESTCOMM PHARMACEUTICAL CO LTD; Shandong Bainuo Pharmaceutical Co., Ltd.; YU YANG; Yu Yang; CHEN JINGJIN; Chen Jingjin; ZHOU HUAYIN; Zhou Huayin; WANG LINYONG; Wang Linyong; ZHANG ZHIQIANG; Zhang Zhiqiang; SUN YUANJUN; Sun Yuanjun; QIU XIN; Qiu Xin; WANG YULIANG; Wang Yuliang; (16 pag.)CN108299480; (2018); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

13726-14-2, A common heterocyclic compound, 13726-14-2, name is 4-Chloro-3-methoxyaniline, molecular formula is C7H8ClNO, 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 2(1-Benzyl-piperidin-4-yl)-(4-chloro-3-methoxy-phenyl)-amine/V-Benzylpiperidone (7.9 ml_, 43,8 mmol), 4-chloro-3-methoxy-phenylamine (6.9 g, 43.8 mmol) and sodium sulphate (31.1 g, 218 mmol) were suspended in dichloromethane (250 ml_). Sodium triacetoxyborohydride (11.4 g, 52.5 mmol) was added and the reaction mixture was stirred at room temperature overnight.Aqueous sodium hydrogencarbonate was added followed by stirring for 30 min.The mixture was extracted with dichloromethane and the combined organic phases were washed with brine, dried over sodium sulphate, filtrated and concentrated in vacuo. (1 -Benzyl-piperidin-4-yl)-(4-chloro-3-methoxy-phenyl)- amine was precipitated from ethyl acetate/heptane 6.7 g (46%) as a white solid.

The synthetic route of 13726-14-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NEUROSEARCH A/S; WO2009/77585; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

4863-91-6, 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.

2,5-Hexanedione (4.51 mL) and p-toluenesulfonic acid monohydrate (73 mg) were added to a solution of 3-chloro-5-fluoroaniline (5.12 g) in toluene (40 mL)-tetrahydrofuran (40 mL), and the mixture was heated under reflux for 3.5 hours. After being cooled down, the reaction solution was concentrated in vacuo, and the resultant residue was dissolved in chloroform. The solution was washed successively with water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The resulted residue was purified by column chromatography on silica gel (Solvent: n-hexane/ethyl acetate = 97/3) to give the titled compound (7.63 g) as a yellow oil. APCI-MS m/z:224/226[M+H]+

According to the analysis of related databases, 4863-91-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; EP2179994; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics