Category: chlorides-buliding-blocks

Application of 33786-89-9, These common heterocyclic compound, 33786-89-9, name is 5-Chloro-m-phenylenediamine, 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.

(1) To a solution of 5-chloro-1,3-phenylenediamine (2.00 g) in acetic acid (20 mL) was added 2,5-dimethoxytetrahydrofuran (1.8 mL). After 4 hours at reflux, the reaction mixture was concentrated. The residue was suspended in satd. NaHCO3 and EtOAc. The reaction mixture was filtered and the organic layer was collected, washed with satd. NaHCO3 and brine, dried (Na2SO4), filtered and concentrated. Purification of the residue by chromatography (silica gel: EtOAc/hexane: 1/4) afforded 0.54 g of 3-chloro-5-(1-pyrrolyl)aniline. MS (m/z) 193 (MH+).

Statistics shows that 5-Chloro-m-phenylenediamine is playing an increasingly important role. we look forward to future research findings about 33786-89-9.

Reference:
Patent; TANABE SEIYAKU CO., LTD.; EP1307455; (2005); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 108-70-3, name is 1,3,5-Trichlorobenzene, 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 108-70-3, Application In Synthesis of 1,3,5-Trichlorobenzene

General procedure: Aryl chloride (1.0 mmol),arylboronic acid (1.2 mmol), precatalyst (0.05 mmol), preligand (0.05 mmol),and base (3.0 mmol) were added to a Schlenk tube equipped with a magnetic stirring bar, a septum, and a reflux condenser. After the tube was evacuated and refilled with nitrogen gas three times, degassed solvent (3 mL) was added via a syringe. The reaction mixture was heated to the described temperature for the required time. After the reaction cooled to room temperature, water (10 mL) was added tothe reaction mixture. The resulting mixture was extracted with CH2Cl2(3 x 10 mL). The combined organic layers were dried over anhydrous Na2SO4,filtered and concentrated to dryness. The remaining residue was analyzed by GC(Table 1) or purified by flash chromatogram phy on silica gel with ethylacetate-hexanes (0-20% ethyl acetate in hexanes) of as eluents.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,3,5-Trichlorobenzene, and friends who are interested can also refer to it.

Reference:
Article; Hu, Feng; Kumpati, Blessy N.; Lei, Xiangyang; Tetrahedron Letters; vol. 55; 52; (2014); p. 7215 – 7218;,
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. 106-39-8, name is 1-Bromo-4-chlorobenzene, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 1-Bromo-4-chlorobenzene

General procedure: A 50 mL round-bottomed flask, equipped with a gas inlet tube, a refluxcondenser and a magnetic stirring bar was charged with MCM-41-2PPdCl2 (102 mg, 0.05 mmol Pd), aryl halide (5.0 mmol) and HCOONa(7.5 mmol). The flask was flushed with CO. DMF (5 mL) was addedby syringe and a slow stream of CO was passed into the suspension.The mixture was vigorously stirred at 110-130 C for 2-20 h, cooledto room temperature and diluted with diethyl ether (50 mL). Thepalladium catalyst was separated from the mixture by filtration,washed with distilled water (2 ¡Á 10 mL), ethanol (2 ¡Á 10 mL) and ether(2 ¡Á 10 mL) and reused in the next run. The ethereal solution waswashed with water (3 ¡Á 20 mL), and dried over anhydrous magnesiumsulfate and concentrated under reduced pressure. The residue waspurified by flash column chromatography on silica gel (hexane-ethylacetate = 10 : 1).

According to the analysis of related databases, 106-39-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Jiang, Jianwen; Wang, Pingping; Cai, Mingzhong; Journal of Chemical Research; vol. 38; 4; (2014); p. 218 – 222;,
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. 27139-97-5, name is 2-Bromo-4-chloro-1-methylbenzene, This compound has unique chemical properties. The synthetic route is as follows., category: chlorides-buliding-blocks

An agitator provided, 200 ml of a Schlenk tube substd. argon, as shown in the above-mentioned chemical eq. (116) 2-bromo-4-chlorotoluene (5. 02g, 20. A 0mmol) and diethyl ether (50 ml), stirring, -15 ¡ã C are cooled. There, 1. ¡¤ Phenylbicyclohexane soln. 6M-n-butyl lithium (13. 0 ml, 20. 5mmol) is dropped. 1 period, trimethyl borate (2. 13g, 20. 5mmol) is added, while warming up to a room temperature, a cooling bath is removed from 15¡ã C-, 18 hours. By adding distilled water (20 ml) little by little, the reaction is stopped, and diethyl ether Phenylbicyclohexane under reduced pressure is removed.

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 27139-97-5.

Reference:
Patent; NIPPON HOSO KYOKAI <NHK>; KANTO CHEM CO INC; FUKAGAWA HIROHIKO; SHIMIZU TAKAHISA; TAKAHASHI JUNPEI; SHINNAI SATONOBU; TSUCHIYA KAZUHIKO; (53 pag.)JP2015/160849; (2015); A;,
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. 104-11-0, name is 1-(4-Chlorophenyl)-N-methylmethanamine, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 1-(4-Chlorophenyl)-N-methylmethanamine

General procedure: A solution of 0.17g (1.40mmol) of N-benzylmethylamine, 0.20g (1.40mmol) of K2CO3 and 0.40g of (R,S)-3(4-bromobutyl)-5-phenyloxazolidin-2-one 23 in ACN was allowed to stirring under reflux for 6-12h and monitored by TLC until the reaction was completed. The hot solution was filtered and concentrated in vacuo to afford 0.29g (85.0mmol) of a chromatography pure yellow oil 2a.

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 104-11-0.

Reference:
Article; Zampieri, Daniele; Vio, Luciano; Fermeglia, Maurizio; Pricl, Sabrina; Wuensch, Bernhard; Schepmann, Dirk; Romano, Maurizio; Mamolo, Maria Grazia; Laurini, Erik; European Journal of Medicinal Chemistry; vol. 121; (2016); p. 712 – 726;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 27139-97-5,Some common heterocyclic compound, 27139-97-5, name is 2-Bromo-4-chloro-1-methylbenzene, molecular formula is C7H6BrCl, 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.

1) Preparation of 4-[3-(2-bromo-4-chlorobenzyl)-4,4-dimethyl-2,5-dioxoimidazolidin-1-yl]-2-trifluoromethylbenzonitrile 109.2Compound 109.2 was prepared as described for example 1.2, by reacting compound 1.1, instead of 2-bromobenzyl bromide, with 2-bromo-1-bromomethyl-4-chlorobenzene (prepared by N-bromosuccinimide bromination from 2-bromo-4-chloro-1-methylbenzene; 1H NMR: 7.82, d, 1H; 7.65, s, 1H, 7.5, d, 1H, 4.72, s, 2H). 4-[3-(2-Bromo-4-chlorobenzyl)-4,4-dimethyl-2,5-dioxoimidazolidin-1-yl]-2-trifluoromethylbenzonitrile was obtained. (Molecular weight 498.99 (C20H14BrClF3N3O2); retention time Rt=2.30 min. [B]; MS (ESI): 541.04 (MH++CH3CN).

The synthetic route of 27139-97-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANOFI-AVENTIS; US2009/215728; (2009); 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. 367-22-6, name is 4-Chloro-3-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 367-22-6

To 4-chloro-3-fluoroaniline (25g, 0.17 mmol) in 250 mL of H2O was added NaHCO3 (21.6g, 0.25 mmol). After cooling to 0 C, iodine (43.5g, 0.17 mmol) was added. After 18 h at rt, an additional 10.8 g of iodine was added and the reaction was stirred overnight. The reaction was extracted with DCM (4×250 mL), the combined organics were washed with sodium thiosulfate solution (2×250 mL) and brine (2×250 mL) and dried (Na2SO4). Purification by silica gel chromatography gave 47 g of Intermediate 5A.MS (ESI) m z: 145.2 (M+H)+.

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 367-22-6.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; ORWAT, Michael J.; PINTO, Donald J.P.; SMITH II, Leon M.; SRIVASTAVA, Shefali; WO2013/56034; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 452-83-5, 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. 452-83-5, name is 2-Chloro-5-fluoroaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A solution of ethyl 4,4,4-trifluoroacetoacetate (commercially available, 4 mL, 27.3 mmol, 1.05 eq.) in polyphosphoric acid (22 mL) was heated to 1000C. 2-chloro-5- fluoroaniline (3.78 g, 26.0 mmol, 1 eq.) was added slowly to the stirred hot solution. The resulting reaction mixture was further heated to 1500C and then stirred at that temperature overnight (approximately 18 hours). The reaction was cooled to room temperature and water was added carefully. The resulting light brown precipitate was collected by vacuum filtration, washed with water and dissolved in ethyl acetate. The ethyl acetate solution was washed with brine, dried over anhydrous MgSO4 and concentrated on a rotary evaporator. The crude product was purified by flash chromatography on silica gel using hexane/ethyl acetate to give 3.54 g (51% yield) of the desired product as an off- white solid; MP = 141-142; MS (ES) m/z (relative intensity): 266 (M+H)+ (100).

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-Chloro-5-fluoroaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; WYETH; WO2007/146072; (2007); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 33863-76-2, 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. 33863-76-2 name is 1-Bromo-3-chloro-5-fluorobenzene, 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.

Sodium methoxide (4.5M solution in methanol, 2.20 [ML,] 10.0 [MMOL)] was added dropwise to a stirred solution of 1-fluoro-3-chloro-5-bromobenzene (1.00 g, 4.77 [MMOL)] in methanol (28 [ML)] at room temperature under a nitrogen atmosphere. The mixture was heated at reflux for 3 days and then cooled to room temperature. The mixture was evaporated under reduced pressure and the resulting yellow oil was dissolved in [DICHLOROMETHANE] (30 [ML).] The [DICHLOROMETHANE] solution was washed with water [(2X20] [ML)] dried over magnesium sulphate, filtered and evaporated under reduced pressure. The residue was purified by chromatography on silica gel eluting with cyclohexane to provide the title compound as a colourless oil (302 mg). [1 H-NMR (400MHZ, CDC13)] : [8] 3.77 (s, 3H), 6.82 (s, 1 H), 6.94 (s, 1 H), 7.09 (s, [1 H).] Microanalysis : Found: C, 37.94 ; H, 2.75. [C7H6BRCIO] requires ; C, 37.96 ; H, 2.73%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-3-chloro-5-fluorobenzene, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER LIMITED; PFIZER INC.; WO2004/29051; (2004); 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. 918538-05-3, name is 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine, This compound has unique chemical properties. The synthetic route is as follows., name: 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine

General procedure: To a solution of 2,4-dichlorofuro[3,2-d]pyrimidine (la) (0.71 g, 3.74 mmol; CAS 956034- 07-4) in 2-Propanol (20 mL) was added DIPEA (1.63 mL, 9.36 mmol), 1-methyl-1H-imidazol-4-amine hydrochloride (0.5 g, 3.74 mmol) and heated at reflux for 24 h. The reaction mixture was concentrated in vacuum to dryness and the residue obtained was triturated with water. The solid obtained was collected by filtration and dried in vacuum to afford 2-chloro-N-(l-methyl-lH-imidazol-4-yl)furo[3,2-d]pyrimidin-4-amine (lb) (550 mg,59 % yield) as brown solid; NMR (300 MHz, DMSO-^) delta 10.89 (s, 1H, D20exchangeable), 8.35 (d, J = 2.1 Hz, 1H), 7.52 (d, J = 1.6 Hz, 1H), 7.39 (d, J = 1.3 Hz, 1H), 7.03 (d, J = 2.1 Hz, 1H), 3.71 (s, 3H); MS (ES+): 250.3 (M+l), 272.3, 274.3 (M+Na), (ES-): 248.2 (M-l).

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 918538-05-3.

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