Category: chlorides-buliding-blocks

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. 50638-46-5, name is 4-Bromo-3-chloroanisole, This compound has unique chemical properties. The synthetic route is as follows., Safety of 4-Bromo-3-chloroanisole

A mixture of 1 -bromo-2-chloro-4-methoxybenzene (1.5 g, 6.8 mmol), oxazole (878 mg, 12.7 mmol), /-BuOK (1.52 g, 13.5 mmol) and tetrakis (1.56 g, 1.35 mmol) in dioxane (10 mL) was heated to 100C under N2 atmosphere for 4 hr. After cooling to r.t., the reaction mixture was concentrated under reduced pressure to give the crude product which was purified by flash chromatography (silica gel, 0 to 25% EA in PE) to afford 2-(2-chloro-4-methoxyphenyl)oxazole (40) (600 mg, 42 % yield) as a yellow solid. LC-MS (ESI): mlz (M+l) 210.0.

According to the analysis of related databases, 50638-46-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PHARMACYCLICS LLC; CHEN, Wei; WANG, Longcheng; YAN, Shunqi; LOURY, David, J.; JIA, Zhaozhong, J.; FRYE, Leah, Lynn; GREENWOOD, Jeremy, Robert; SHELLEY, Mee, Yoo; ATALLAH, Gordana, Babic; ZANALETTI, Riccardo; CATALANI, Maria, Pia; RAVEGLIA, Luca, Francesco; (402 pag.)WO2016/4272; (2016); A1;,
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Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 13078-79-0, 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. 13078-79-0, name is 2-(3-Chlorophenyl)ethanamine, This compound has unique chemical properties. The synthetic route is as follows.

Triethylamine (153 muL, 1.10 mmol) was added dropwise at 0 C to a stirred suspension of 2-(1H-indol-3-yl)-2-oxoacetyl chloride (5; 208 mg, 1.00 mmol) and 2-(3-chlorophenyl)ethylamine (139 muL, 1.00 mmol) in anhydrous tert-butyl methyl ether (20 mL). The reaction mixture was stirred at 0 C for 15 min and then for 1 h at room temperature, monitoring the reaction by TLC analysis. After completion of the reaction the mixture was washed with a saturated NaHCO3 aqueous solution and water (3 × 20 mL in each case). The organic layer was dried over anhydrous Na2SO4 and evaporated. Recrystallization of the crude product from ethanol 70% yielded colourless crystals (33%).Mp.: 184-186 C; IR (KBr): 3347 cm-1 and 3190 cm-1 (NH), 2938 cm-1 (CH aliph.), 1657 cm-1 (CO); 1H NMR (DMSO-d6, 400.1 MHz): delta (ppm) = 2.88 (t, 2H, J = 7.0 Hz, NHCH2CH2), 3.50 (dt, 2H, J = 6.4/6.8 Hz, NHCH2CH2), 7.21-7.34 (m, 6H, ar-H), 7.52-7.57 (m, 1H, ar-H), 8.21-8.27 (m, 1H, ar-H), 8.67 (s, 1H, ar-H), 8.81 (t, 1H, J = 5.8 Hz, NH), 12.24 (s, 1H, indole-NH); 13C NMR (DMSO-d6, 100.6 MHz): delta (ppm) = 34.2 (CH2), 39.2 (CH2); 112.5, 121.2, 122.5, 123.4, 126.1, 127.5, 128.5, 130.1, 138.4 (tert. C); 112.1, 132.9, 136.3, 141.9, 163.6, 182.1 (quat. C, one signal is missing due to peak overlap); C18H15ClN2O2 (326.78); calcd. C 66.16, H 4.63, N 8.57; found C 65.84, H 4.60, N 8.31; HPLC-purity: 99.3% at 254 nm and 98.9% at 280 nm, tN = 3.38 min, tM = 1.03 min (ACN/H2O; 55:45), lambdamax: 256 nm and 327 nm.

The chemical industry reduces the impact on the environment during synthesis 2-(3-Chlorophenyl)ethanamine. I believe this compound will play a more active role in future production and life.

Reference:
Article; Schmidt, Stefanie; Preu, Lutz; Lemcke, Thomas; Totzke, Frank; Schaechtele, Christoph; Kubbutat, Michael H.G.; Kunick, Conrad; European Journal of Medicinal Chemistry; vol. 46; 7; (2011); p. 2759 – 2769;,
Chloride – Wikipedia,
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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. 367-22-6, name is 4-Chloro-3-fluoroaniline, A new synthetic method of this compound is introduced below., Formula: C6H5ClFN

To a solution of 4-chloro-3-fluoroaniline (15 g, 103.05 mmol) in dichloromethane (150 mL) was added ICl (25 g, 154.57 mmol) drop wise. The resulting black mixture was stirred at 24-29C for 2h. The mixture was diluted with 100 mL dichloromethane and washed with saturated solution of sodium bicarbonate (200 mL). The organic layer was concentrated to give the crude residue, which was purified by flash column chromatography on silica gel (0 to 0.5%ethyl acetate in Petroleum ether) to afford compound 41a (8 g brown solid and 12 g black solid, 71.5% yield in total). LCMS: R t = 0.974 min in 5-95AB_220&254 chromatography (MERCK RP18 2.5-2mm), MS (ESI) m/z = 271.8 [M+H] +. 1H NMR: (400MHz, CDCl 3) delta 7.53 (d, J = 8.0 Hz, 1H), 6.46 (d, J = 10.4 Hz, 1H), 4.12 (s, 2H).

The synthetic route of 367-22-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DIZAL (JIANGSU) PHARMACEUTICAL CO., LTD; LI, Zhengtao; ZOU, Hao; ZHU, Wei; SHEN, Changmao; WANG, Rumin; LIU, Wengeng; CHEN, Xiang; TSUI, Honchung; YANG, Zhenfan; ZHANG, Xiaolin; (307 pag.)WO2019/149164; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 14862-52-3, name is 3,5-Dibromochlorobenzene, 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 14862-52-3, Safety of 3,5-Dibromochlorobenzene

3-cyanophenyl boronic acid (25.0 g, 0.17 mol) and 1,3-dibromo-5-chlorobenzene (23.0 g, 0.08 mol) Dissolved in 290 mL of tetrahydrofuran, 1.5 M aqueous potassium carbonate solution (90 mL) was added,Tetrakis- (triphenylphosphine) palladium (3.94 g, 0.34 mmol) was added thereto, followed by heating with stirring for 13 hours.The temperature was lowered to room temperature, the water layer was separated off, dried over anhydrous magnesium sulfate and concentrated under reduced pressureRecrystallization was performed using chloroform and ethanolWas dried to prepare the intermediate n (44.7 g, yield 83%).

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

Reference:
Patent; LG Chem, Ltd.; Lee Jeong-ha; Moon Jeong-uk; Jeong Min-u; Lee Dong-hun; Chae Mi-yeong; (49 pag.)KR2018/32517; (2018); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 7149-75-9, 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. 7149-75-9, name is 4-Chloro-3-methylaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: The corresponding pyrazinoic acid (5.0 mmol) was dispersed in dry toluene (20 mL) and mixed with 1.5eq. of thionyl chloride (0.55 mL, 7.5 mmol). The reaction mixture was heated to reflux for approximately 1 h. Next, the excess of thionyl chloride was removed by repeated evaporation with dry toluene under vacuum.The crude acyl chloride was dissolved in dry acetone(20 mL) and added drop-wise to a stirred solution of the corresponding aniline (5.0 mmol) with triethylamine(5.0 mmol) in dry acetone (30 mL). The reaction mixture was stirred at ambient temperature for up to 6 h. The completion of the reaction was monitored by TLC (eluent: hexane/ethyl acetate; r =2 : 1). The crude product adsorbed on silica gel by solvent evaporation was purified by flash chromatography(hexane/ethyl acetate gradient elution).The analytical data of the prepared compounds were fully consistent with the proposed structures and are available in the Supplementary Data.

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, 4-Chloro-3-methylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zitko, Jan; Barbora, Servusova-Vanaskova; Paterova, Pavla; Navratilova, Lucie; Trejtnar, Frantisek; Kunes, Jiri; Dolezal, Martin; Chemical Papers; vol. 70; 5; (2016); p. 649 – 657;,
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. 2401-24-3, name is 2-Chloro-5-methoxyaniline, A new synthetic method of this compound is introduced below., COA of Formula: C7H8ClNO

Preparation of (2-Chloro-5-methoxy-phenyl)-urea (Intermediate 5) A solution of 2-chloro-5-methoxyaniline (5 g, 25.76 mmol) and potassium cyanate (5.22 g, 64.41 mmol) in a mixture of acetic acid (125 mL) and water (12.5 mL) was stirred at room temperature overnight. The solvent was evaporated, and the residue taken into a mixture of CH2Cl2 and an aqueous saturated solution of NaHCO3. The layers were separated, the aqueous one being extracted three times with CH2Cl2. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated. The crude material was purified by flash chromatography on silica gel (cyclohexane/EtOAc/MeOH: 80/20/2) to give 2.06 g (40%) of intermediate 5. 1H NMR [(CD3)2SO] delta7.97 (br s, 1H, NH), 7.85 (d, J=3.0 Hz, 1H), 7.27 (d, J=9.0 Hz, 1H), 6.54 (dd, J=9.0, 3.0 Hz, 1H), 6.4-(br s, 2H), 3.71 (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; Bernardelli, Patrick; Ducrot, Pierre; Lorthiois, Edwige; Vergne, Fabrice; US2002/198198; (2002); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 2770-11-8, name is 2-(4-Chlorophenoxy)aniline, molecular formula is C12H10ClNO, 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. Quality Control of 2-(4-Chlorophenoxy)aniline

A stirred solution of Boc-glycine (1.50 mmol), PyBOP (1.60 mmol) and DIPEA (3.50 mmol) in dichloromethane (10 mL) was cooled to 0 C with an ice bath. To this solution 2-(4-chlorophenoxy)aniline (1.50 mmol), dissolved in a minimum amount of dichloromethane, was added dropwise. The reaction mixture was allowed to warm to room temperature and was then stirred for 24 h. Thereafter, an aqueous work-up was performed similar to that of compounds 1-8. The resulting oil was further purified by column chromatography over silica gel(dichloromethane/methanol 200:1) to give a slightly orange solid (358 mg, 0.95 mmol, 63%); m.p.: 50-51 C; IR (KBr): [cm-1] nu = 3409 (m, N-H), 3342 (s, N-H), 1691 (br, s, C=O); 1H-NMR: (600 MHz, DMSO-d6): delta [ppm] = 1.34 (s, 9H, CH3), 3.71 (d, J = 6.1 Hz, 2H, CH2), 6.87-7.06 (m, 3H, arom. H), 7.05-7.30 (m, 3H, arom. H), 7.35-7.53 (m, 2H, arom. H), 8.12 (d, J = 7.7 Hz, 1H, NH), 9.33 (s, 1H, NH); 13C-NMR (151 MHz, DMSO-d6) delta [ppm] = 28.00 (3C, CH3), 43.92 (CH2), 118.82, 119.90 (2C), 122.35, 124.15, 124.63, 129.70 (2C) (CH), 78.17, 127.17, 129.64, 146.09, 155.47, 155.86, 168.51 (C); EI-MS: m/z (%): 376.1 [M]+ (11), 219.1 [M – 157]+ (100); HREI-MS: calcd. for C19H21ClN2O4 376.11844, found 376.11803; HPLC: 96.3% at 254 nm, 96.3% at 280 nm; tR = 4.84 min, tM(DMSO) = 1.06 min(ACN/H2O = 60:40), lambdamax [nm] = 230; HPLC-gradient: 95.8%, tR = 12.80 min, tM(DMSO) = 1.28 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2770-11-8, its application will become more common.

Reference:
Article; Weidner, Thomas; Nasereddin, Abed; Preu, Lutz; Gruenefeld, Johann; Dzikowski, Ron; Kunick, Conrad; Molecules; vol. 21; 2; (2016);,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

19752-55-7, name is 1-Bromo-3,5-dichlorobenzene, belongs to chlorides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. SDS of cas: 19752-55-7

After mixing compound 3-3 (10 g, 0.02 mol), 1-bromo-3,5-dichlorobenzene (7.2 g, 0.03 mol), tetrakis(triphenylphosphine)palladium(O) (0.92 mg, 0.79 mmol), sodium carbonate (5.6 g, 0.05 mol), toluene 130 mL, ethanol 33 mL, and distilled water 33 mL in a flask, the mixture was stirred at 120°C for 12 hours. After completing the reaction, the mixture was extracted with ethylacetate, and the obtained organic layer was dried with anhydrous magnesium sulfate and filtered. The solvent was then removed under reduced pressure, and the remaining substance was subjected to column chromatography to separate compound 3-4 (4.4 g, 35percent).

The synthetic route of 19752-55-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD.; AHN, Hee-Choon; YANG, Soo-Jin; MOON, Doo-Hyeon; JUN, Ji-Song; LEE, Tae-Jin; LEE, Kyung-Joo; KWON, Hyuck-Joo; KIM, Bong-Ok; WO2014/98518; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 1127-85-1, 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. 1127-85-1, name is 2,4-Dichloro-5,6,7,8-tetrahydroquinazoline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of 2,4-dichloropyrrolo[1,2-f][1,2,4]triazine (4a) (0.5 g, 2.7 mmol) in 2-Propanol (6 mL) was added (S)-pyrrolidin-2-ylmethanol (0.39 mL, 4.0 mmol), DIPEA (1.39 mL, 8.0 mmol) and heated at 90 C for 1 hr. The reaction was cooled to room temperature and solid obtained was collected by filtration to afford (S)-(l-(2-chloropyrrolo[2,l-f][l,2,4]triazin-4- yl)pyrrolidin-2-yl)methanol (96a) (0.49 g, 73 % yield) as a white solid; NMR (300 MHz, DMSO-i/e): delta 7.70 (dd, J= 2.6, 1.4 Hz, 1H), 6.97 (dd, J= 4.7, 1.6 Hz, 1H), 6.80 – 6.57 (m, 1H), 5.15 (t, J = 5.7 Hz, 1H, D2O exchangeable), 4.87 (t, J= 5.7 Hz, 1H), 4.44 (d, J= 17.8 Hz, 1H), 4.05 – 3.82 (m, 1H), 3.72 – 3.39 (m, 2H), 2.22 – 1.84 (m, 4H). MS (ES+): 253.3, 255.3 (M+2); MS (ES-): 287.2, 289.2 (M+Cl).

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, 2,4-Dichloro-5,6,7,8-tetrahydroquinazoline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BIOCRYST PHARMACEUTICALS, INC.; KOTIAN, Pravin, L.; BABU, Yarlagadda, S.; KUMAR, V., Satish; ZHANG, Weihe; LU, Peng-Cheng; RAMAN, Krishnan; (747 pag.)WO2018/232094; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 32768-54-0, These common heterocyclic compound, 32768-54-0, name is 2,3-Dichlorotoluene, 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 1L reactor,add 61.5 g of 2,3-dichlorotoluene, 3.075 g of azobisisobutyronitrile (5%), 215.25 g of 2-dichloroethane, heat the mixture at 75 C and add 44 g of bromine drop wise,reflux reaction till red bromine fades , Intermittent drip and 136.2g27.5% hydrogen peroxide continues to react till red bromine no longer generates. Add a 49.2g30% aqueous solution of sodium carbonate to the reaction solution, reflux reaction for 8 h ,at the same time recover1,2-dichloroethane.

Statistics shows that 2,3-Dichlorotoluene is playing an increasingly important role. we look forward to future research findings about 32768-54-0.

Reference:
Patent; Lianyungang Industry Investment Group Co., Ltd.; Jiang Honglai; Jiang Xiao; Han Yong; Zang Han; Zhu Chengjie; Shen Weiwei; (5 pag.)CN107032968; (2017); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics