Month: August 2021

Adding a certain compound to certain chemical reactions, such as: 445-13-6, name is 3-Chloro-4-(trifluoromethyl)aniline, 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 445-13-6, Computed Properties of C7H5ClF3N

To a suspension of calcium carbonate (1.04 g, 10.4 mmol, Eq: 2.03) and thiophosgene (645 mg, 430 mu, 5.61 mmol, Eq: 1.1) in dichloromethane (13.2 g, 10.0 ml, 155 mmol, Eq: 25.3)/water (10.0 g, 10.0 ml, 555 mmol, Eq: 90.2) at 0, was added 3-chloro-4- (trifluoromethyl)aniline (1 g, 5.11 mmol, Eq: 1.00) The reaction was gradually warmed to room temperature and stirred overnight. Added 10 mL IN HC1. Separated organic layer, dried over sodium sulfate, and chromatographed (60 g Analogix, 100% hex) to give 962 mg (79%) of desired product as colorless oil.

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

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BILOTTA, Joseph Anthony; CHEN, Zhi; CHIN, Elbert; DING, Qingjie; ERICKSON, Shawn David; GABRIEL, Stephen Deems; KLUMPP, Klaus; MA, Han; MERTZ, Eric; PLANCHER, Jean-Marc; WEIKERT, Robert James; WO2014/6066; (2014); A1;,
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Related Products of 821-10-3, These common heterocyclic compound, 821-10-3, name is 1,4-Dichlorobut-2-yne, 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: K2CO3 (3a, 210 mg, 1.5 mmol) was added to a solution of b-ketosulfones 1a-p (0.5 mmol) in acetone (10 mL) at 25 C. The reaction mixture was stirred at 25 C for 10 min. 1,4-Dichloro-2-butyne (2, 68 mg, 0.55 mmol) was added to the reaction mixture at 25 C. The reaction mixture was stirred at 56 C for 8 h. The reaction mixture was cooled to 25 C and the solvent was concentrated. The residue was diluted with water (10 mL) and the mixture was extracted with CH2Cl2 (320 mL). The combined organic layers were washed with brine, dried, filtered and evaporated to afford crude product. Purification on silica gel (hexanes/EtOAc15/1e8/1) afforded 4a-p.

The synthetic route of 821-10-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chan, Chieh-Kai; Lu, Yi-Ju; Chang, Meng-Yang; Tetrahedron; vol. 71; 51; (2015); p. 9544 – 9549;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

17318-08-0, name is 5-Bromo-1,3-dichloro-2-fluorobenzene, 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. Recommanded Product: 5-Bromo-1,3-dichloro-2-fluorobenzene

1-(3,5-dichloro-4-fluorophenyl)-2,2,2-trifluoroethan-1-one (Intermediate Compound 9) (0328) (0329) 9 (0330) [0164] To a cooled (10 C) solution of 1-bromo-3,5-dichloro-4-fluorobenzene (1.10 kg, 4.51 mol) in THF (9.70 L) was added /-PrMgCI LiCI (3.64 L, 4.74 mol, 1.3 molar) while maintaining the internal temperature at < 20 C. The reaction was stirred for 2 hours with an internal temperature of 18 C, before cooling to - 9 C. Methyl trifluoroacetate (499 ml_, 4.96 mol) was added while maintaining the internal temperature < 10 C. Reaction was warmed to 20 C and stirred for 3 hours before it was quenched with 4 molar HCI (1.50 L). The biphasic mixture was stirred 2 hours before it was diluted with heptane (4 L). The reaction was mixed for 10 min. and the layers allowed to separate. The aqueous layer was removed extracted 1X 2 L EtOAc and the combined organic fractions were washed 1 X 4L 22% aq. NaCI and dried over MgS04 (1.5 kg) for 15 hours. The organic solution was filtered and concentrated in vacuo. The residue was dissolved in toluene (4 L) and concentrated in vacuo. The resultant oil was dissolved in toluene (4 L) and concentrated in vacuo a second time to give 1.06 kg of 1-(3,5-dichloro-4-fluorophenyl)-2,2,2-trifluoroethan-1-one (89%) that was 91% pure. (0331) [0165] Note that the yields for smaller scale reactions have ranged between 60 - 94% for this experiment. (0332) [0166] 1H NMR (400MHz, CHLOROFORM-d) delta = 8.06 (dd, J=0.8, 6.1 Hz, 2H). (0333) [0167] Note that the hemiacetal hydrate can be detected in the 1H NMR as a doublet at delta = (0334) 7.69. The synthetic route of 17318-08-0 has been constantly updated, and we look forward to future research findings. Reference:
Patent; AVISTA PHARMA SOLUTIONS, INC.; SPEAKE, Jason, D.; PANDI, Bharathi; OGBU, Cyprian, O.; ADAMS, Jeffrey, A.; MOORE, III, Joseph, A.; PERALAS, Joe, B.; LI, Keqiang; (50 pag.)WO2017/201134; (2017); 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 1939-99-7 as follows. Application In Synthesis of Phenylmethanesulfonyl chloride

To a solution of 2-((tert-butyldimethylsilyl)oxy)ethanamine (11.7 g, 66.6 mmol) and triethylamine (11.2 mL, 79.9 mmol) in tetrahydrofuran (222 mL) at 0 C was slowly added phenylmethanesulfonyl chloride (12.7 g, 66.6 mmol) portion wise and the reaction was stirred at room temperature for 16 hours. MTBE was then added and the Et3N-HCl salt was removed by filtration. The filtrate was then concentrated and purified by silica gel solumn chromatography (0-30% Acetone in heptane, 216 nM) to A^-(2-((tert-butyldimethylsilyl)oxy)ethyl)-l-phenylmethanesulfonamide (17.8 g, 81 % yield). LCMS (ESI), m/z, 330. [M+H] +.

According to the analysis of related databases, 1939-99-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; FAUBER, Benjamin; GANCIA, Emanuela; LADDUWAHETTY, Tammy; VESEY, David; WINSHIP, Paul; RENE, Olivier; (168 pag.)WO2017/5900; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 2533-69-9, 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. 2533-69-9 name is Methyl 2,2,2-trichloroacetimidate, 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 1,2-benzenediamine (2.6 g, 24 mmol) in acetic acid (60 mL), methyl 2,2,2-trichloroethanimidoate (3.1 mL, 25 mmol) was added dropwise at 10 C. The mixture was stirred at room temperature for 5 h, then poured into water (1.0 L). The precipitate was separated by filtration, air-dried, and was directly used for the next step without purification (4.75 g, 84%).

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

Reference:
Patent; Incyte Corporation; Zou, Ge; Combs, Andrew P.; Buesking, Andrew W.; (62 pag.)US2016/229843; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 14752-66-0, name is Sodium 4-chlorobenzenesulfinate, 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 14752-66-0, name: Sodium 4-chlorobenzenesulfinate

General procedure: A mixture of sulfinic acid sodium salt 2 (0.60 mmol), PdCl2 (0.10 equiv), Baylis-Hillman adduct 1 (0.50 mmol), and CuCl2 (1.0 equiv) was dissolved in 1,4-dioxane (3.0 mL) in a 10-mL round- bottomed flask. The mixture was vigorously stirred at 90C for 8 h. After cooling to r.t., the mixture was partitioned between EtOAc (25.0 mL) and H2O (25.0 mL) and filtered through a celite pad. The filtrate was transferred to a separatory funnel, and the organic layer was washed with H2O and brine, dried (anhyd Na2SO4), and concentrated in vacuo. The resulting residue was purified by column chromatography (gradient, hexane-EtOAc) to afford the pure product.

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

Reference:
Article; Bal Raju, Kammari; Mari, Vellakkaran; Nagaiah, Kommu; Synthesis; vol. 45; 20; (2013); p. 2867 – 2874;,
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. 2687-12-9, name is Cinnamyl chloride belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of Cinnamyl chloride

General procedure: To a solution of [Ru(Cp*)Cl2]2 (1) (6.2 mg, 1.5 mol%) and K2CO3 (226 mg, 1.63 mmol) in dry acetonitrile (0.5 mL) in a schlenk tube was added cinnamyl chloride (92 mul, 0.65 mmol). The resulting mixture was stirred at room temperature under a nitrogen atmosphere for 20 min followed by a slow addition of the corresponding phenols (0.98 mmol) (Table 2) in dry acetonitrile (1 mL) over 15 minutes. The reaction mixture was stirred for another 16 h at room temperature and then filtered through a celite plug and washed with dichloromethane (10 mL). The filtrate was evaporated under reduced pressure and purified by silica gel column chromatography to afford the branched product. Characterization data and copies of NMR spectra were provided below

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

Reference:
Article; Siddappa, Ravi Kumara Guralamatta; Chang, Chih-Wei; Chein, Rong-Jie; Tetrahedron Letters; vol. 55; 5; (2014); p. 1031 – 1035;,
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. 766545-20-4, name is 2-Chloro-5,6,7,8-tetrahydro-1,6-naphthyridine hydrochloride, This compound has unique chemical properties. The synthetic route is as follows., category: chlorides-buliding-blocks

Following the procedure described in Example 12,Was reacted with 0.84 g (0.0075 mmol) of N-cyanoethyl ester from 1.03 g (0.005 mol) of 2-chloro-5,6,7,8-tetrahydro-1,6-naphthyridine hydrochloride,To give 0.8 g of a white solid, A mixture of 1.2 g (0.004 mol) of 2-chloro-4,5,6,7-tetrahydrothiazole [5,4-c] pyridine trifluoroacetate,0.67 g (0.006 mol)N-cyanoethyl esterWas added to a reaction flask equipped with 30 ml of methanol,0.73 g (0.0048 mol) of DBU was added,Heating to reflux reaction,After 2 hours the TLC monitoring reaction was complete,Cooling white solid precipitation,

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 766545-20-4.

Reference:
Patent; Shenyang Sinochem Pesticide Chemical Research and Development Co., Ltd.; Yang, Jichun; Li, Miao; Fan, Xiaoxi; Yang, Fan; Li, Keke; Liu, Zhangling; (46 pag.)CN106467538; (2017); A;,
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. 1939-99-7, name is Phenylmethanesulfonyl chloride, A new synthetic method of this compound is introduced below., Application In Synthesis of Phenylmethanesulfonyl chloride

To a solution of 2-((tert-butyldimethylsilyl)oxy)ethanamine (11.7 g, 66.6 mmol) and triethylamine (11.2 mL, 79.9 mmol) in tetrahydrofuran (222 mL) at 0 C. was slowly added phenylmethanesulfonyl chloride (12.7 g, 66.6 mmol) portion wise and the reaction was stirred at room temperature for 16 hours. MTBE was then added and the Et3N.HCl salt was removed by filtration. The filtrate was then concentrated and purified by silica gel solumn chromatography (0-30% Acetone in heptane, 216 nM) to N-(2-((tert-butyldimethylsilyl)oxy)ethyl)-1-phenylmethanesulfonamide (17.8 g, 81% yield). LCMS (ESI), m/z, 330. [M+H]+.

The synthetic route of 1939-99-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Genentech, Inc.; Fauber, Benjamin; Gobbi, Alberto; Rene, Olivier; van Niel, Monique Bodil; Gancia, Emanuela; Gaines, Simon; Ladduwahetty, Tammy; Vesey, David; Ward, Stuart; Winship, Paul; (101 pag.)US2016/168141; (2016); 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. 1205-71-6, name is 4-Chloro-N-phenylaniline, A new synthetic method of this compound is introduced below., Formula: C12H10ClN

General procedure: 0.248 g (1.00 mmol) of (4-bromophenyl) phenylamine, 0.176 g (1.05 mmol) of 9H-carbazole,4.6 mg (5.0 mumol) of tris (dibenzylideneacetone) dipalladium,14.9 mg (35.0 mumol) of 2- (di-tert-butylphosphino) -2 ‘, 4′, 6′-triisopropyl-1,1’-biphenyl,After 0.144 g (1.50 mmol) of sodium tert-butoxide and 3 mL of o-xylene were added, the inside of the reaction system was replaced with argon gas.Thereafter, the mixture was heated to 140 C. and stirred for 15 hours. After cooling to room temperature, the reaction was stopped by adding 25 mL of water. Further, 20 mL of ethyl acetate and 9- (p-tolyl) -9H-carbazole as an internal standard were added and stirred until the ethyl acetate layer became homogeneous.The ethyl acetate layer (0.2 mL) was collected, diluted with tetrahydrofuran 4 mL, and the conversion of (4-bromophenyl) phenylamine was 99% or more by HPLC analysis,It was confirmed that 98% of 9- [4- (phenylamino) phenyl] -9H-carbazole was formed relative to (4-bromophenyl) phenylamine.

The synthetic route of 1205-71-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SAGAMI CHEMICAL RESEARCH INSTITUTE; TOSOH CORPORATION; YAMAKAWA, TETSU; OHTSUKA, YUKI; MIYAZAKI, TAKANORI; (28 pag.)JP2018/90563; (2018); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics