Category: chlorides-buliding-blocks

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. 53531-69-4, name is (4-Bromophenyl)methanesulfonyl chloride, A new synthetic method of this compound is introduced below., Application In Synthesis of (4-Bromophenyl)methanesulfonyl chloride

General procedure: Two-step one-pot method: Add bromobenzyl mercaptan to acetonitrile, then add chlorinating reagent, monitor with spot plate, and transfer to ice water bath after reaction.Add 4 equivalents of an acid binding agent such as pyridine.After slowly adding 7-amino-N-propylquinolinone in acetonitrile,The plate is monitored for reaction, after the reaction, pickling, drying,Further, the abscisic acid receptor agonist can be obtained by column chromatography or recrystallization,

The synthetic route of 53531-69-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shaoyang University; Huang Zhiyou; (7 pag.)CN109678797; (2019); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 2106-04-9, name is 3-Chloro-2-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 2106-04-9, Safety of 3-Chloro-2-fluoroaniline

Step 1: 6-Acetoxy-4-(3-chloro-2-fluoroanilino)-7-methoxycluinazoline hydrochloride6-Acetoxy-7-methoxyquinazolin-4-one (International Patent Application WO 96/15118, Example 39 thereof; 21.4 kg, 89.3 mol) was suspended in toluene (150 kg). To this was added N-ethyldiisopropylamine (13.3 kg, 103 mol). The brown suspension was heated to 70 C. then phosphorus oxychloride (36.0 kg, 228 mol) was charged. The reaction mixture was stirred at 70 C. for 5 hours. Further toluene (84.0 kg) was added followed by 3-chloro-2-fluoroaniline (14.88 kg, 102 mol). The reaction mixture was stirred at 70 C. for 2 hours during which time a solid precipitated. The suspension was cooled to 25 C. and held at this temperature for 93 hours. The reaction mixture was filtered and the filter cake washed with toluene (2×55.5 kg). The cake was further washed with a mixture of ethanol (24.5 kg) and water (32.0 kg) twice, then ethanol (50.5 kg) twice and the solid then dried under vacuum to give the title product as a beige solid (33.4 kg, 78%); 1H NMR: 2.37 (s, 3H), 4.00 (s, 3H), 7.34 (ddd, 1H), 7.48 (s, 1H), 7.52 (ddd, 1H), 7.61 (ddd, 1H), 8.62 (s, 1H), 8.86 (s, 1H); Mass Spectrum: 362.4, 364.4.

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-fluoroaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; US2009/286982; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 1996-30-1, 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. 1996-30-1 name is 3-Bromo-4-fluorochlorobenzene, 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.

General procedure: 1.00 mmol arylhalide, 1.30 mmol furfural-boronic acid and 0.05 mmolBis(triphenylphosphine)palladium(II) dichloride were treated with 0.30 mLdimethoxyethane, 0.50 mL ethanol and 0.30 mL aqueous 2M sodium carbonate solution.The reaction was heated to 65C for 1h or until the TLC showed no remaining startingmaterial. The mixture was evaporated and extracted three times with ethyl acetate. Thecombined organic layers were washed with brine, dried over MgSO4, filtered andconcentrated. The crude product was purified by column chromatography usinghexanes/ethyl acetate (9:1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Bromo-4-fluorochlorobenzene, and friends who are interested can also refer to it.

Reference:
Article; Krake, Susann H.; Martinez, Pablo David G.; McLaren, Jenna; Ryan, Eileen; Chen, Gong; White, Karen; Charman, Susan A.; Campbell, Simon; Willis, Paul; Dias, Luiz Carlos; European Journal of Medicinal Chemistry; vol. 126; (2017); p. 929 – 936;,
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. 461432-23-5, name is 4-Bromo-1-chloro-2-(4-ethoxybenzyl)benzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C15H14BrClO

Synthesis of compound 63C35H36F206/ C35H34F205I9F NMR (CDCU. 282.5MHz):Hydrate form: -1 17.3 (dd, Jl=257Hz, J2=30Hz, IF, CFF); -125.6 (d, Jl=258Hz, IF, CFF).Ketone form: -112.1 (ddd, Jl=260Hz, J2=32Hz, J3=6Hz, IF, CFF); -119.4 (dd, Jl=260Hz, J2=4Hz, IF, CFF).ass (ESf): 608.4 [M+H20]+; 613.5 [M+Na]+; 619.5 [M+K]+ To a solution of 62 (200mg; 0.35mmol; leq) in dry dichloromethane, under inert atmosphere, was added Dess-Martin periodinane (295mg; 0.70mmol; 2eq). The reaction medium was stirred for 3h at room temperature before a IN aqueous solution of sodium hydroxide (lOmL) was added. The aqueous layer was extracted with dichloromethane and dried over sodium sulphate, filtered and concentrated to afford ketone 63 (158mg, 77% yield) as a light orange solid which rapidly evolves toward the formation of the hydrate form until equilibrium is reached.Synthesis of compound 64C50H49CIF2O6 M=819.37g.mor1 19 F NMR fCDCk 282.5MHz): -1 12.3 (dd, Jl=266Hz, J2=27Hz, IF, CFF); -113.7 (dd, Jl=266Hz, J2=6Hz, IF, CFF).Mass (ESf): 836.7[M+H20]+; 841.8[M+Na]+; 857.7[M+K]+ In a Schlenk tube under inert atmosphere containing magnesium turnings (50mg, 2.04mmol, 1.2eq) was added 2inL (out of 5mL) of a solution of 10 (552mg, 1.70mmol, leq) and 1,2-dibromoethane (15mu, 0.17mmol, O. leq) in dry THF (5mL). The mixture was heated at 75C for 5 min to initiate the reaction and the last 3mL of the solution of 10 and 1,2-dibromoethane were then added dropwise at room temperature. This solution was then stirred at 75C for lh.2.4mL of this Grignard solution, previously cooled to room temperature, were then added to a solution of 63 (158mg, 0.27mmol) in dry THF (2mL). The reaction mixture was stirred at room temperature for 2h before a saturated aqueous solution of ammonium chloride was added. The aqueous layer was extracted with diethyl ether and the combined organic layers were washed with brine, dried over sodium sulphate, filtered and concentrated. The residue was purified on silica gel chromatography (cyclohexane/ethyl acetate 100:0 to 77:23) to afford compound 64 (152mg) as a mixture of two diastereomers with 69% yield. These diastereomers can be separated by semi- preparative HPLC.

The synthetic route of 461432-23-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TFCHEM; DELIENCOURT-GODEFROY, Geraldine; LOPES, Lenaig; WO2012/160218; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 2106-02-7,Some common heterocyclic compound, 2106-02-7, name is 2-Chloro-4-fluoroaniline, molecular formula is C6H5ClFN, 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.

A mixture of (S)-1-(1-(3-chlorophenyl)-2-hydroxyethyl)-3-(1-(2-chloropyrimidin-4-yl)-1H-pyrazol-4-yl)urea (0.02 g, 0.05 mmol), 2-chloro-4-fluoroaniline (0.009 g, 0.6 mmol), potassium carbonate (0.01 g, 0.075 mmol), and dioxane (2 mL) in a glass tube was purged with nitrogen gas for 20 min. Tris(dibenzylideneacetone)dipalladium(0) (0.002 g, 0.0025 mmol) and BINAP (0.003 g, 0.005 mmol) were added to the reaction mixture, which was purged with nitrogen gas for another 15 min. The tube was sealed and heated at 90 C. for 4 hours. Reaction mixture was filtered through Celite, and filtrate was evaporated; residue was suspended in water, and extracted with ethyl acetate. Organic layer was dried over sodium sulfate, evaporated, and the residue was purified by column chromatography over silica gel using 60% ethyl acetate in hexanes as eluent to give (S)-1-(1-(2-((2-chloro-4-fluorophenyl)amino)pyrimidin-4-yl)-1H-pyrazol-4-yl)-3-(1-(3-chlorophenyl)-2-hydroxyethyl)urea (0.003 g, 12%). 1HNMR (400 MHz, CDCl3, plus a few drops MeOD): 8.50 (s, 1H), 8.33 (d, J=5.2 Hz, 1H), 8.27-8.25 (m, 1H), 7.51 (s, 1H), 7.28-7.19 (m, 1H), 7.23-7.12 (m, 3H), 7.12-7.10 (m, 1H) 7.04-6.99 (m, 1H), 6.23 (d, J=6.8 Hz, 1H) 4.87-4.84 (m, 1H), 3.81-3.77 (m, 1H), 3.64-3.61 (m, 1H). LC-MS calcd exact mass 501.09, found m/z 502.3 [M+H]+. HPLC purity 98.17%.

The synthetic route of 2106-02-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Asana Biosciences, LLC; Venkatesan, Aranapakam M.; Thompson, Scott K.; Smith, Roger A.; Reddy, Sanjeeva P.; (166 pag.)US2016/362407; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 2687-12-9, A common heterocyclic compound, 2687-12-9, name is Cinnamyl chloride, molecular formula is C9H9Cl, 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 1Obtaining 2- (3-N,N-diisopropylamine-l-phenylpropyl) -A- carboxyphenol (IVa)(IVa) Diisopropylamine (2.77 1, 19.65 mol) and sodium iodide(16.95 g, 0.13 mol) were loaded onto a solution of cinnamyl chloride (1 kg, 6.55 mol) in ethanol (3 I/kg) at 20/250C. The mixture was heated at internal 80-850C, the reaction conditions being maintained for 3-4 hours until the end of such reaction.The mixture was cooled at 40-450C and distilled to an internal volume of 1.3 1. The mixture was then cooled at 20- 25C, water (4 1) and toluene (3 1) was added and the pH was adjusted to 1.0-1.5. The phases were decanted and dichloromethane (4 1) was loaded onto the aqueous phase, adjusting the pH again to 11.5-12.0. The phases were decanted and the organic phase was washed with water (4 1) . Once the phases were decanted, the organic phase was distilled at atmospheric pressure to an internal volume of 1.3 1 in order to then load heptane (0.5 1) . Again, it was distilled to 1.3 1 and heptane (2 1) was loaded.The suspension which was obtained was filtered by a prelayer, which was washed with heptane (0.5 1) . The filtered organic phase was distilled at atmospheric pressure to an internal volume of 1.3 1.The amine content of the reaction mixture was determined by the potentiometric titration thereof.

The synthetic route of 2687-12-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RAGACTIVES, S.L.U.; LORENTE BONDE-LARSEN, Antonio; MARTIN PASCUAL, Pablo; LADERAS MUNOZ, Mario; GUTIERREZ FUENTES, Luis Gerardo; WO2011/12584; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 3972-56-3, These common heterocyclic compound, 3972-56-3, name is 1-tert-Butyl-4-chlorobenzene, 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.

100 ml of 60% nitric acid was added dropwise to 100 ml of 95% sulfuric acid at a temperature of 35C or less, under ice-cooling, to prepare a mixed acid solution. 100 g (0.593 mol) of 4-tert-butylchlorobenzene (A-1) was added dropwise to this mixed acid solution, at a temperature of 30C or less, followed by after-reaction (20 to 25C) for 2.5 hours. The reaction solution was poured into cold water, and it was then extracted with 100 ml of toluene, followed by washing with water, to obtain a toluene solution of (A-2).

The synthetic route of 3972-56-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FUJI PHOTO FILM CO., LTD.; EP1535898; (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. 104-52-9, name is 3-Phenylpropyl Chloride, This compound has unique chemical properties. The synthetic route is as follows., Safety of 3-Phenylpropyl Chloride

6-amino-1-ethylbenzo[cd]indol-2(1H)-one can refer to Example 1. A reaction mixture of 6-amino-1-ethylbenzo[cd]indol-2(1H)-one (100 mg, 0.47 mmol) and (3-chloropropyl)benzene (73 mg, 0.47 mmol) in CH3CN (20 mL) was stirred at rt. K2CO3 (195 mg, 1.41 mmol) was added to the reaction mixture, and stirred at 70 C. for overnight. The reaction mixture was extracted with ethyl acetate (150 mL*2). The organic layer was washed with brine and dried over Na2SO4. The solid was filtered off, and the filtrate was concentrated under reduced pressure. The resulting crude product was purified by silica gel chromatography with petroleum ether/ethyl acetate (5/1, v/v) to yield 1-ethyl-6-((3-phenylpropyl)amino)benzo[cd]indol-2(1H)-one (60 mg, 38%) as a yellow solid. 1H NMR (400 MHz, CDCl3) delta 8.06 (d, J=7.2 Hz, 11H), 7.84 (d, J=8.0 Hz, 1H), 7.63 (t, J=7.6 Hz, 1H), 7.32 (t, J=7.6 Hz, 2H), 7.26-7.04 (m, 3H), 6.77 (d, J=7.6 Hz, 1H), 6.34 (d, J=7.2 Hz, 1H), 4.24 (s, 1H), 3.94 (q, J=7.2 Hz, 2H), 3.30 (t, J=6.8 Hz, 2H), 2.83 (t, J=7.2 Hz, 2H), 2.21-2.03 (m, 2H), 1.36 (t, J=7.2 Hz, 3H).

According to the analysis of related databases, 104-52-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Guangzhou Institutes of Biomediciene and Health, Chinese Academy of Sciences; XU, Yong; XUE, Xiaoqian; ZHANG, Yan; SONG, Ming; (42 pag.)US2018/8574; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 51572-93-1,Some common heterocyclic compound, 51572-93-1, name is O-(2,4-Dichlorobenzyl)hydroxylamine hydrochloride, molecular formula is C7H8Cl3NO, 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: To a solution of 3ae3e (1 mmol) in anhydrous ethanol (10 mL),corresponding O-benzylhydroxylamine hydrochloride (1 mmol)and NaOAc (1.2 mmol) were added and the resulting solution wasstirred at the room temperate for 3 h. The mixture was concentratedand taken in ethyl acetate (20 mL), washed with water(20 mL), saturated sodium chloride solution (20 mL) and dried oversodium sulfate. The resulting solution was concentrated and thepurification of the residue by recrystallization from ethanol yieldedthe desired compounds 4a-4t

The synthetic route of 51572-93-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lv, Xian-Hai; Li, Qing-Shan; Ren, Zi-Li; Chu, Ming-Jie; Sun, Jian; Zhang, Xin; Xing, Man; Zhu, Hai-Liang; Cao, Hai-Qun; European Journal of Medicinal Chemistry; vol. 108; (2016); p. 586 – 593;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 118-69-4, The chemical industry reduces the impact on the environment during synthesis 118-69-4, name is 2,6-Dichlorotoluene, I believe this compound will play a more active role in future production and life.

To a mixed solution of compound 39-a-1 (5 g, 31.06 mmol), iron powder (87 mg, 1.55 mmol) and iodine (39mg, 0.15 mmol) in carbon tetrachloride was added dropwise bromine (5.22 g, 32.61 mmol) at room temperature. Afterthe addition was complete, the reaction solution was stirred at room temperature for two days. The reaction solutionwas quenched with sodium bisulfite solution, extracted with dichloromethane (2*50 ml), and the organic phase waswashed with saturated brine (30 ml), concentrated and dried to give compound 39-a (4.77 g) as a colorless oil directlyused in the next reaction, purity 76%, yield 64%, MS m/z(ESI):N/A.

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, 2,6-Dichlorotoluene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shanghai Haiyan Pharmaceutical Technology Co., Ltd.; Yangtze River Pharmaceutical Group Co., Ltd.; LAN, Jiong; ZHOU, Fusheng; ZHAO, Jinzhu; HUANG, Dong; XIE, Jing; HU, Yi; LV, Qiang; (63 pag.)EP3412653; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics