Category: chlorides-buliding-blocks

Synthetic Route of 13726-14-2, 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. 13726-14-2 name is 4-Chloro-3-methoxyaniline, 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 solution of 4-chloro-3-methoxy-aniline (7.00 g, 44.4 mmol) dissolved in dichloromethane (100 mL) at 5 C was treated portions with NBS (8.14 g, 45.7 mmol) over 1 hour, then warmed to 20 C and stirred at 20 C for 2 hours. On completion, a 5% aqueous Na2SO3 solution (100 mL) was added and the mixture was stirred for 10 minutes. The layers were separated and the organic layer was washed with water and saturated brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The getting residue was purified by column chromatography (petroleum ether: ethyl acetate = 3:1) to give the title compound (9.00 g, 85% yield) as a dark brown solid.1H NMR (400MHz, CD3Cl) delta = 7.37 (s, 1H), 6.35 (s, 1H), 4.13 (br. s., 2H), 3.83 (s, 3H).

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

Reference:
Patent; RAZE THERAPEUTICS, INC.; MAINOLFI, Nello; (215 pag.)WO2018/106636; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 210532-25-5, 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 210532-25-5 as follows.

To a mixture of 3-({3-[(tetrahydro-pyran-4-yl)-(2,2,2-trifluoro-acetyl)-amino]-pyridine- 4-carbonyl}-amino)-5,6-dihydro-4H-pyrrolo[3,4-c]pyrazole-l-carboxylic acid ethyl ester hydrochloride (0.75 mmol), dry dichloromethane (50 mL) and triethylamine (0.84 mL, 6 mmol) was added 3,5-difluorobenzenesulfonyl chloride (478 mg, 2.25 mmol). The mixture was stirred at room temperature for 4 hours then methanol (10 mL) and triethylamine (5 mL) were added. The mixture was then heated to 600C and the stirring continued for 2 hours. The solvents were evaporated and the crude residue purified by flash chromatography on silica gel, affording the title compound as pale yellow solid (100 mg). IH-NMR (400 MHz), delta (ppm, DMSOtZ6): 12.59, 12.35 (2s, IH), 11.04, 11.02 (2s, IH), 8.87, 8.82 (2s, IH), 7.93, 7.86 (2m, IH), 7.71-7.52 (m, 4H), 7.28 (d, IH), 4.61, 4.52 (2s, 2H), 3.86 (m, 2H), 3.81 (m, IH), 3.50 (m, 2H), 1.98 (m, 2H), 1.68, 1.64 (2s, 6H), 1.44 (m, 2H), mixture of tautomers

According to the analysis of related databases, 210532-25-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NERVIANO MEDICAL SCIENCES S.r.l.; WO2007/68637; (2007); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 30273-47-3,Some common heterocyclic compound, 30273-47-3, name is 4-Bromo-5-chloro-2-methylaniline, molecular formula is C7H7BrClN, 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 95 Preparation of 4-bromo-2,3-dichloro-6-methylaniline This material was prepared from 4-bromo-5-chloro-2-methylaniline by chlorination with N-chlorosuccinimide. The product was isolated as a solid, m.p. 66-68 C. The product was characterized by IR and 1 H NMR spectroscopy and combustion analysis.

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

Reference:
Patent; The Dow Chemical Company; US4818273; (1989); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 13726-14-2,Some common heterocyclic compound, 13726-14-2, name is 4-Chloro-3-methoxyaniline, molecular formula is C7H8ClNO, 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 3: Preparation of N-(4-Chloro-3-methoxyphenyl)-l-(4-methoxybenzyl)-lH- yrazolof 4, 3-b]pyridin-3-amine (Exp- 1 -g4)[0088] Into a vessel containing 1.5 mL dioxane was placed 63 mg of the crude Exp-1- g3 prepared in Step 2 (0.2 mmol). To the vessel was added 39 mg of 4-chloro-3- methoxy-phenylamine (0.25 mmol), 18 mg Pd2dba3 (0.02 mmol), 23 mg Xantphos (0.04 mmol) and 130 mg Cs2C03 (0.4 mmol). The reaction mixture thus provided was refluxed under a nitrogen atmosphere for 4 hours, then filtered and concentrated under reduced pressure. The residue was subjected to Prep-TLC (PE:EtOAc = 2: 1) to obtain Exp-l-g4 (52 mg, 66 %).

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

Reference:
Patent; MERCK SHARP & DOHME CORP; ADDEX PHARMA S.A.; LIVERTON, Nigel; JONES, Philip; BOLEA, Christelle; CELANIRE, Sylvain; TANG, Lam; BOUDOU, Cedric; LEI, Zhiyu; LIU, Fuqing; LUO, Yunfu; DONG, Jingchao; SOLL, Richard; WO2013/60029; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 14752-66-0, 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. 14752-66-0, name is Sodium 4-chlorobenzenesulfinate, This compound has unique chemical properties. The synthetic route is as follows.

A method for preparing a distyryl sulfide compound, comprising the steps of:0.3mmol (0.0541g)1,1-stilbene, 0.45 mmol (0.0894 g) of sodium p-chlorobenzenesulfinate and 0.2558 g of a 45% by mass aqueous solution of hydroiodic acid (containing 0.9 mmol of hydroiodic acid) were dispersed in 2 mL of toluene. The coupling reaction was carried out at 75 C for 15 h, quenched with a saturated aqueous solution of sodium thiosulfate, and extracted with dichloromethane (15 mL×3).The liquid layer was separated, and the organic layer was dried over anhydrous sodium sulfate.Dry under reduced pressure, and the column was passed to give 0.0812 g of distyryl thioether compound (white solid, yield 84%)

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

Reference:
Patent; South China Normal University; Guangdong Pharmaceutical University; Wang Chaoyang; Wang Bowen; Zou Bo; Zhan Haiying; (17 pag.)CN110305051; (2019); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 328-84-7, These common heterocyclic compound, 328-84-7, name is 3,4-Dichlorobenzotrifluoride, 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.

The procedure of Example 4 was repeated but using 3,4-dichlorobenzotrifluoride. After work up there was isolated a 95% yield of the title compound. It was shown that 100% of the starting material had been consumed, thus indicating that the reaction had occurred with both high selectivity and high yield.

Statistics shows that 3,4-Dichlorobenzotrifluoride is playing an increasingly important role. we look forward to future research findings about 328-84-7.

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

These common heterocyclic compound, 2267-25-6, name is 2-Chloro-4-fluoroanisole, 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. Safety of 2-Chloro-4-fluoroanisole

2-Chloro-4-fluoro-1-methoxybenzene a8 (0.0160 g, 0.10 mmol), acridine photosensitizer (A) (0.0029 g, 0.005 mmol) and L-valine were added sequentially under argon atmosphere. Ethyl b1 (0.0218 g, 0.15 mmol), 1,2-dichloroethane (DCE) 2.0 mL.The reaction was irradiated for 48 hours under a 6W blue light at room temperature.After completion of the reaction, the solvent was evaporated under reduced pressure and purified by column chromatography, eluting solvent: (V) petroleum ether / (V) ethyl acetate = 20/1.A yellow liquid (25) (0.0191 g, 87%) was obtained.

The synthetic route of 2-Chloro-4-fluoroanisole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Central China Normal University; Zhou Shaolin; Shi Weimin; (27 pag.)CN110294685; (2019); A;,
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 6940-78-9 as follows. Computed Properties of C4H8BrCl

Add potassium carbonate (9.42 g) in water (10ml) in round bottom flask and stirred for 10-15 min at 30-35C. To this add DMF (50ml) and 7-Hydroxy quinolin-2(lH)-one (10g), heated the resulting mixture to 35-40C and stirred for 10-15 min. To this added 1-Bromo-4-chloro butane (21.29 g) and stirred the reaction mass for 6-8 hours at 35-40C, added water (20ml) drop wise over a period of 30-40 minutes and stirred the reaction mass for 30-40 min at 35-40C. Cooled the reaction mass to 10C, filtered and washed with methanol (20 ml) and DM water (20 ml) at 25-30C to obtain wet material. Yield: 11.0 g, HPLC purity- 95.8%; Dimer Impurity: 1.49% To the resulting wet material (11.0 g), methanol (200ml) was added at 25-30C and heated to reflux till complete dissolution. To this added AMBER LITE IR 120 H (10g) at 65-70C and stirred for 1-1.5 hours at reflux temperature. Filtered the resulting mixture through hyflo at 60-65C and cooled the filtrate to 5-10C and stirred for 30 minutes. Filtered the material, washed with methanol (10 ml) and dried at 60-65C for 5-8 hours. Yield: 8.0 g, HPLC purity: 97.3%; Dimer impurity: 0.027%.

According to the analysis of related databases, 6940-78-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JUBILANT GENERICS LIMITED; BANSAL, Deepak; MISHRA, Himanchal; MISHRA, Vaibhav; SRIVASTAVA, Alka; VIR, Dharam; (24 pag.)WO2017/216661; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 13918-92-8, 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. 13918-92-8, name is 2,4-Difluorobenzene-1-sulfonyl chloride belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a stirred solution of 5-bromo-2-methoxypyridin-3-amine 1 (13.70 g, 67.5 mmol) in pyridine (140 mL) was added dropwise 2,4-difluorobenzenesulfonyl chloride 2 (14.35 g, 67.5 mmol) over 10 min at 0 C. The mixture, which quickly became heterogeneous, was allowed to warm to ambient temperature and stirred for 16 h, at which time the reaction was diluted with water (400 mL) and the solids were filtered and washed with water. The precipitate was dried in a vacuum oven at 60 C to give N-(5-bromo-2-methoxypyridin-3-yl)-2,4-difluorobenzenesulfonamide 3 (18.30 g, 71.3% yield) as a pale yellow powder, which was used without further purification.

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-Difluorobenzene-1-sulfonyl chloride, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Han, Jinsong; Chen, Ying; Yang, Chao; Liu, Ting; Wang, Mingping; Xu, Haojie; Zhang, Ling; Zheng, Canhui; Song, Yunlong; Zhu, Ju; European Journal of Medicinal Chemistry; vol. 122; (2016); p. 684 – 701;,
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. 7051-16-3, name is 1-Chloro-3,5-dimethoxybenzene, A new synthetic method of this compound is introduced below., Computed Properties of C8H9ClO2

General procedure: A 0.94 M soln of MeMgBr in THF (1.59 mL, 1.5 mmol) was added to a mixture of FeF3 (5.7 mg, 0.050 mmol) and 1,3-bis(2,6-diisopropylphenyl)imidazolinium chloride (64.4 mg, 0.15 mmol) in THF (2.0 mL) at 0C; 1-chloro-4-methoxybenzene (143 mg, 1.0 mmol) and undecane were then added at r.t. The mixture was stirred at 80 C for 24 h. The mixture was cooled to r.t. and an aliquot of the mixture was filtered through a Florisil pad. The product yield was determined by GC analysis (92% yield) using undecane as an internal standard. 1-Methoxy-4-methylbenzene is volatile, hence isolation was performed for the large-scale experiment using starting aryl chloride (5.6 mmol). The crude product was purified by column chromatography (silica gel, pentane, Rf = 0.06) and subsequent GPC to obtain the title compound (78.7 mg, 11%) as a colorless oil.

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; Agata, Ryosuke; Iwamoto, Takahiro; Nakagawa, Naohisa; Isozaki, Katsuhiro; Hatakeyama, Takuji; Takaya, Hikaru; Nakamura, Masaharu; Synthesis; vol. 47; 12; (2015); p. 1733 – 1740;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics