Category: chlorides-buliding-blocks

Electric Literature of 627-42-9, 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. 627-42-9 name is 2-Methoxyethyl chloride, 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.

To a solution of 6 (3.4 g, 20 mmol) in N,N?-dimethylformamide (DMF), K2CO3 (5.5 g, 40 mmol) was added at room temperature. After the mixture was stirred at 90 oC for 10 minutes, the DMF solution (2 mL) of 1-chloro-2-methoxyethane (3.8 g, 40 mmol) was slowly added over the course of 30 min at this temperature. The mixture was stirred at 90 oC for 12 h. After completion of the reaction, the mixture was poured into ice water (60 mL), followed by extraction with ethyl acetate (60 ¡Á 3 mL). The combined organic solvent phase was then washed by water (60 ¡Á 3 mL) and saturated sodium chloride (60 ¡Á 3 mL), dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to afford an oil, which was purified by column chromatography with petroleum ether/ethyl acetate (10 : 1) to obtain 7. Methyl 2-hydroxy-4-(2-methoxyethoxy)benzoate (7) White solid, yield 91%; mp: 136-138 oC; 1H NMR (CDCl3, 600 MHz): delta = 7.73 (1H, d, J = 8.4 Hz, H-6), 6.48 (1H, dd, J = 1.8, 8.4 Hz, H-5), 6.46 (1H, d, J = 1.8 Hz, H-3), 4.82 (1H, br, ArOH), 4.13 (2H, t, J = 4.8 Hz, ArOCH2), 3.91 (3H, s, COOCH3), 3.75 (2H, t, J = 4.8 Hz, CH3OCH2), 3.45 (3H, s, CH3OCH2); HRMS (ESI) m/z calcd. for C11H14O5 ([M+H]+): 227.0914, found: 227.0913.

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

Reference:
Article; Liu, Yang; Li, Yijing; Liu, Jianzhen; Yang, Limin; Li, Pengzhan; Zhao, Guisen; Letters in drug design and discovery; vol. 13; 4; (2016); p. 314 – 323;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 367-21-5, 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 367-21-5 as follows.

(1) 145.6 g (1.00 mol) of 3-chloro-4-fluoroaniline were dissolved in a mixture of 330 ml of 48% strength hydrobromic acid and 330 ml of water and diazotized by adding a solution of 70.4 g (1.02 mol) of sodium nitrite in 220 ml of water dropwise at 5 C. The diazonium salt solution thus obtained was added dropwise to a mixture of 188 g (1.3 mol) of copper(I) bromide and 400 ml of 48% strength hydrobromic acid at 30-40 C. After conclusion of gas evolution, the produce was extracted using three 300 ml portions of hexane. The extracts were washed twice with 5N sodium hydroxide solution and once with water, dried over sodium sulfate and evaporated. The residue yielded 187.2 g (89%) of 4-bromo-2-chlorofluorobenzene of b.p.10 =73-75 C. with a purity >99% (determined by gas chromatography) on subsequent distillation.

According to the analysis of related databases, 367-21-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hoechst Aktiengesellschaft; US4920212; (1990); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 89794-02-5, name is 4-Bromo-2-chlorotoluene, 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 89794-02-5, Product Details of 89794-02-5

Example P14: Preparation of 2-(4-bromo-2-chlorophenyl)-1-methyl-ethylamine (compound no. Z1.451): a) Preparation of 4-bromo-2-chloro-1-dibromomethyl-benzeneA mixture of 4-bromo-2-chlorotoluene (10 g, 48.6 mmol), N-bromosuccinimide (43.3 g, 243.3 mmol), benzoyl peroxide (0.5 g) and CCI4 (80 ml) was heated to reflux for 6 h. Completion of the reaction was confirmed by TLC. After cooling a yellow precipitate was isolated by filtration and washed with CCI4. The organic layer was concentrated and both the concentreated organic layer and the precipitate were purified by chromatography using silica column (60-120 mu mesh) and hexane as eluent. 17.5 g (98% of theory) of 4-bromo-2-chloro- 1-dibromomethyl-benzene was obtained. 1HNMR (400 MHz, CDCI3):- 7.02 delta (s, 1 H), 7.5 delta (dd, 2H), 7.87 delta (d,1H,CHBr2),

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; SYNGENTA PARTICIPATIONS AG; SYNGENTA LIMITED; WO2007/141009; (2007); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 626-43-7, 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. 626-43-7, name is 3,5-Dichloroaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To the 250 mL reaction flask was added solid phosgene (13.8 g, 0.046 mol) (purchased from Zhejiang Lishui Yibang Chemical Co., Ltd., purity 99%, the same hereinafter) and toluene (60 g), and 3,5-dichloroaniline (16.2 g, 0.1 mol) (Purity: 99%, the same as below) with triethylamine (1.0 g, 0.01 mol) (purchased from Beijing Chemical Reagent Co., Ltd., purity: 99%, same as below) and toluene (40.0 g) was added dropwise at a temperature of 48 ¡À 2 C for about 45 min.The temperature was raised to 75 C and incubated for 4 hours. and then continue to heat up to 110 C and heat 3 hours, the sample monitoring to 3,5-dichloroaniline content of less than 0.5%, cooling to 60 C, and the introduction of nitrogen to eliminate excess phosgene and hydrochloric acid gas reaction. To give toluene solution A1 (114.5 g, w / w = 15.7%) of 3,5-dichlorophenyl isocyanate in a yield of 95.6%.

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

Reference:
Patent; Beijing Yingtai Jiahe Biotechnologies Co Ltd; Wang, Wenjun; Jin, Wentao; Yu, Huimei; Ma, Jinyong; Yang, Dazhi; (12 pag.)CN103539744; (2016); B;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 5719-08-4, name is 4-Chloro-9H-pyrimido[4,5-b]indole belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C10H6ClN3

3.9. 4,6-Dichloro-9-(2,3,5-tri-O-benzoyl-b-D-ribofuranosyl)-pyrimido[4,5-b]indole (13) : Pyrimidoindole 11 (200 mg, 0.84 mmol) was suspended in acetonitrile (5 ml) and BSA (206 ll, 0.84 mmol) was added. Reaction mixture was stirred for 10 min at rt., TMSOTf (308 ll, 1.68 mmol) and protected ribofuranose (430 mg, 0.84 mmol) were added. Mixture was heated to 60 C for 8 h. After cooling to rt, the mixture was extracted with EtOAc and water, organic layer was washed with NaHCO3 and again with water, dried over MgSO4 and evaporated under reduced pressure. Crude product was purified using column chromatography (hexane/EtOAc, 0-40% EtOAc). After crystallization from chloroform/methanol mixture, nucleoside 13 (572 mg, 54%) was observed as white crystals; 3.10 4-Chloro-9-(2,3,5-tri-O-benzoyl-beta-d-ribofuranosyl)-pyrimido[4,5-b]indole (14) : Compound 14 was prepared as described for 13 from pyrimidoindole 12 (300 mg, 1.5 mmol) to give 440 mg (46%) of white crystals; mp 178-182 C, IR (ATR): nu = 2360, 2336, 1718, 1546, 1442, 1261, 1090, 1068, 704 cm-1. H NMR (600.1 MHz, DMSO-d6): 4.69 (dd, 1H, Jgem = 12.4, J5’b,4′ = 4.2, H-5’b); 4.85 (dd, 1H, Jgem = 12.4, J5’a,4′ = 3.2, H-5’a); 4.91 (ddd, 1H, J4′,3′ = 6.6, J4′,5′ = 4.2, 3.2, H-4′); 6.36 (t, 1H, J3′,2′ = J3′,4′ = 6.6, H-3′); 6.61 (dd, 1H, J2′,3′ = 6.6, J2′,1′ = 4.6, H-2′); 7.03 (d, 1H, J1′,2′ = 4.6, H-1′); 7.41 (m, 2H, H-m-Bz-2′); 7.50 (m, 4H, H-m-Bz-3′,5′); 7.51 (ddd, 1H, J6,5 = 7.8, J6,7 = 7.3, J6,8 = 1.0, H-6); 7.57 (ddd, 1H, J7,8 = 8.4, J7,6 = 7.3, J7,5 = 1.3, H-7); 7.62 (m, 1H, H-p-Bz-2′); 7.68 (m, 2H, H-p-Bz-3′,5′); 7.84 (m, 2H, H-o-Bz-2′); 7.93 (m, 2H, H-o-Bz-5′); 7.99 (m, 2H, H-o-Bz-3′); 8.10 (ddd, 1H, J8,7 = 8.4, J8,6 = 1.0, J8,5 = 0.7, H-8); 8.35 (ddd, 1H, J5,6 = 7.8, J5,7 = 1.3, J5,8 = 0.7, H-5); 8.78 (s, 1H, H-2). 13C NMR (150.9 MHz, DMSO-d6): 63.1 (CH2-5′); 70.3 (CH-3′); 72.2 (CH-2′); 78.8 (CH-4′); 86.2 (CH-1′); 112.1 (CH-8); 112.4 (C-4a); 118.0 (C-4b); 122.9 (CH-5); 123.3 (CH-6); 128.6, 128.8 (C-i-Bz); 128.9 (CH-m-Bz); 129.0 (CH-7); 129.3 (CH-o-Bz-5′); 129.4 (C-i-Bz); 129.5 (CH-o-Bz-2′); 129.6 (CH-o-Bz-3′); 133.8, 134.1 (CH-p-Bz); 138.4 (C-8a); 152.1 (C-4); 154.0 (C-2-furyl); 154.0 (CH-2); 155.3 (C-9a); 164.8 (COPh-2′); 165.0 (COPh-3′); 165.5 (COPh-5′). ESI MS m/z (rel.%): 670 (100) [M+Na], 672 (33) [M+2+Na]. HR MS (ESI) for C36H27ClN3O7 [M+H]: calcd 648.15320; found 648.15318.

The synthetic route of 5719-08-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tichy, Michal; Pohl, Radek; Hocek, Michal; Xu, Hao Ying; Chen, Yen-Liang; Yokokawa, Fumiaki; Shi, Pei-Yong; Bioorganic and medicinal chemistry; vol. 20; 20; (2012); p. 6123 – 6133,11;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 2106-04-9, A common heterocyclic compound, 2106-04-9, name is 3-Chloro-2-fluoroaniline, molecular formula is C6H5ClFN, 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 suspension of Intermediate 5 (100 g, 0.396 mol) in acetonitrile (4 L) was added 2-fluoro-3-chloroaniline (60.5 g, 0.416 mol) and the reaction mixture was heated to 80 C. overnight. The precipitate was collected by filtration and dried in vacuo to afford Intermediate 6 (181 g, 80% purity) as white solid which was used for next step directly without purification. 1H NMR (DMSO-d6 400 MHz): delta 8.93 (s, 1H), 8.82 (s, 1H), 7.67-7.63 (m, 1H), 7.59 (s, 1H), 7.56-7.52 (m, 1H), 7.39-7.35 (m, 1H), 4.02 (s, 3H), 2.39 (s, 3H).

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:
Patent; ASTRAZENECA AB; LI, David Yunzhi; WANG, Jiabing; YANG, Zhenfan; ZENG, Qingbei; ZHANG, Xiaolin; US2014/255428; (2014); 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 4584-46-7 as follows. HPLC of Formula: C4H11Cl2N

Provided in is step-by-step synthesis of PCA 1 and PCA 2. To make intermediate 3a 4-(2-(dimethylamino)ethoxy)-3-methoxybenzaldehyde, vanillin (1.52 g, 10 mmol), 2-chloro-dimethylethylamine HCI (2.16 g, 15 mmol), potassium iodide (332 mg, 2 mmol) and potassium carbonate (4.14 g, 30 mmol) were suspended in acetone and heated at reflux for 16 h. Next, volatiles were removed in vacuo and the resulting residue is redissolved in water and ethyl acetate. The organic layer was separated and washed with brine and dried with magnesium sulfate. Concentrating in vacuo resulted in 1.75 g (78%) of a yellow oil. NMR and mass spectrometry analysis of intermediate 3a 4-(2-(dimethylamino)ethoxy)-3-methoxybenzaldehyde is provided in to 4C: 1H NMR (400 MHz, Chloroform-d) delta9.82 (s, 1H), 7.41 (dd, J=8.2, 1.9 Hz, 1H), 7.37 (d, J=1.9 Hz, 1H), 6.96 (d, J=8.2 Hz, 1H), 4.17 (t, J=6.1 Hz, 2H), 3.89 (s, 3H), 2.79 (t, J=6.1 Hz, 2H), 2.32 (s, 6H). () 13C NMR (101 MHz, CDCl3) delta191.2, 154.0, 150.0, 130.3, 127.0, 111.7, 109.3, 67.4, 58.0, 56.2, 46.3. () ESI-MS [M+H]: Calculated: 224.1; Observed: 224.1 ()

According to the analysis of related databases, 4584-46-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; The Board of Trustees of the Leland Stanford Junior University; Velema, Willem Arend; Kool, Eric T.; (79 pag.)US2019/264205; (2019); A1;,
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. 39885-50-2, name is 2-Chloro-4-(trifluoromethyl)aniline, A new synthetic method of this compound is introduced below., Computed Properties of C7H5ClF3N

Reference Example 13 7-Benzyloxy-N-[2-chloro-4-(trifluoromethyl)phenyl]-2-(4-methoxybenzyl)-2H-pyrazolo[4,3-d]pyrimidine-5-amine A mixture of 7-(Benzyloxy)-5-chloro-2-(4-methoxybenzyl)-2H-pyrazolo[4,3-d]pyrimidine(53.0 g), 2-chloro-4-(trifluoromethyl)aniline(38.1 g), tris(dibenzylideneacetone)dipalladium(0)(5.10 g), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene(9.66 g)(a compound obtained in Reference Example 12), cesium carbonate(90.7 g) and 1,4-dioxane(1.05 L) was heated under reflux for 16 hours under argon atmosphere. After being cooled to room temperature, ethyl acetate(1 L) was added to the reaction mixture and filtered through Celite. The residue on the Celite was washed with ethyl acetate(1 L) and chloroform(500 mL), the washings were combined with the filtrate, and concentrated under reduced pressure. The resulting residue was crystallized and triturated in ethyl acetate-diethyl ether(1:1) and the crystalline was filtered and washed with ethyl acetate-diethyl ether(1:1). The obtained crystalline was dried to give the titled compound(43.7 g, 58percent yield) as a pale yellow crystalline. mp.189-192¡ãC, MS(APCI)M/z:540/S42[M+H]+.

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:
Patent; Mitsubishi Tanabe Pharma Corporation; EP1903045; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 367-22-6, 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. 367-22-6, name is 4-Chloro-3-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows.

Example; 4-tert-Butyl-N-(4-chloro-5-fluoro-2-iodo-phenyl)-benzenesulfonamide; Step 1:; Iodine (873 mg, 3.44 mmol) was added to a solution of 4-chloro-3-fluoroaniline (500 mg, 3.44 mmol) and potassium hydroxide (193 mg, 3.44 mmol) in N,N-dimethylformamide (?DMF?) (10 mL) and the reaction was stirred at 60 C. for 18 hours. The crude mixture was subsequently partitioned with ethyl acetate (20 mL) and saturated ammonium chloride (20 mL) and the layers separated. The organic layer was washed with saturated ammonium chloride (3¡Á20 mL), dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude material was purified by flash column chromatography (0-50% ethyl acetate in hexanes) to afford the desired iodoaniline (234 mg, 25%).

The chemical industry reduces the impact on the environment during synthesis 4-Chloro-3-fluoroaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; CHEMOCENTRYX, INC.; US2009/5410; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 83121-15-7,Some common heterocyclic compound, 83121-15-7, name is 3,5-Dichloro-2,4-difluoroaniline, molecular formula is C6H3Cl2F2N, 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.

Step 1: Preparation of 1-bromo-3,5-dichloro-2,4-difluorobenzene To a solution of 3,5-dichloro-2,4-difluorobenzenamine (9.9 g, 50.0 mmol) in HBr (200 mL) was added a solution of NaNO2 (3.45 g, 50.0 mmol) in H2O (80 mL) slowly under salt ice-bath, then the mixture was stirred for 2 h, and CuBr (7.15 g, 50.0 mmol) was added at 0 C. The mixture was stirred for additional 2 h, and then poured into water (100 mL), extracted with DCM, dried over NaSO4, filtered and concentrated under reduced pressure. The resulting residue was purified by chromatography over silica gel eluted with PE to give compound 1-bromo-3,5-dichloro-2,4-difluorobenzene (6.2 g, yield 48%) as a colorless oil. 1H NMR (400 MHz, CDCl3): delta 7.49 (t, J=7.2 Hz, 1H) ppm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,5-Dichloro-2,4-difluoroaniline, its application will become more common.

Reference:
Patent; Anacor Pharmaceuticals, Inc.; Eli Lilly and Company; Akama, Tsutomu; Balko, Terry William; Defauw, Jean Marie; Plattner, Jacob J.; White, William Hunter; Winkle, Joseph Raymond; Zhang, Yong-Kang; Zhou, Yasheen; US2013/131016; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics