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. 627-42-9, name is 2-Methoxyethyl chloride, A new synthetic method of this compound is introduced below., category: chlorides-buliding-blocks

Step (i) N-methoxyethyl-N-methylpyrrolidinium chloride, PYR1(2O1)Cl, was synthesized by reacting N-methylpyrrolidine with the appropriate amount of 2-chloroethyl methyl ether. The reagents were firstly dissolved in ethyl acetate and, then, mixed in a reactor. The reaction temperature was set at 70 C forachieving a yield approaching 100% (determined by weighting the obtained precursor after vacuum drying at 100 C overnight) upon 5-6 days heating due to the low kinetics of the reaction (1) [15,17].A white, solid precipitate of PYR1(2O1)Cl was obtained whereas the yellowish liquid phase (e.g., containing impurities generally very soluble in ethyl acetate) was removed by vacuum filtering (paper filter membrane). Finally, the precursor was rinsed 5 times with ethyl acetate.

The synthetic route of 627-42-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Moreno; Montanino; Carewska; Appetecchi; Jeremias; Passerini; Electrochimica Acta; vol. 99; (2013); p. 108 – 116;,
Chloride – Wikipedia,
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Electric Literature of 62356-27-8, The chemical industry reduces the impact on the environment during synthesis 62356-27-8, name is 1-Bromo-3-chloro-2-methylbenzene, I believe this compound will play a more active role in future production and life.

(a) Preparation of 2-bromo-6-chlorobenzylbromide 2-bromo-6-chlorotoluene (20.55 g) and N-bromosuccinimide (19.6 g) were stirred together in carbon tetrachloride (100 ml) under reflux for 22 hours exposure to radiation from an infrared lamp. The resulting solution was cooled in ice, filtered and evaporated to yield the title product which was dissolved in petroleum ether (60-80). Part was recrystallized therefrom as pink needles (8.5 g) and part was recovered by evaporation as a dark orange solid (17.7 g) (total yield 26.2 g. 92%).

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, 1-Bromo-3-chloro-2-methylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shell Oil Company; US4259349; (1981); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 106-39-8, 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 106-39-8 as follows.

General procedure: CS2 (1.3 mmol, 0.07 mL) was added to a stirred solution of KCN (1.1 mmol, 0.07 g) in DMF (1 mL) at room temperature. After 15 min, bromobenzene (1.0 mmol, 0.10 mL), K2CO3 (1.0 mmol, 0.14 g) and CuI (20 mol%, 0.038 g) were added and the mixture stirred at 120 C. Upon reaction completion (TLC, 6.5 h), the mixture was cooled to room temperature, diluted with H2O (1 mL), and extracted with n-hexane/ethyl acetate (1:1, 4 ¡Á 1 mL). The combined organic extracts were concentrated and the residue purified by silica gel column chromatography using n-hexane as eluent to give the pure diphenyldisulfane in 90% (0.098 g) yield.

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; Abbasi, Mohammad; Nowrouzi, Najmeh; Borazjani, Saeedeh Ghassab; Tetrahedron Letters; vol. 58; 45; (2017); p. 4251 – 4254;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 2613-34-5,Some common heterocyclic compound, 2613-34-5, name is 3-Chloro-2,4-difluoroaniline, molecular formula is C6H4ClF2N, 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: The 4-chloro-6, 7, 8-trimethoxyquinazoline (7) (0.4 mmol) and aromatic amines (0.4 mmol) inisopropyl alcohol (5 mL) were stirred at reflux temperature for about 4 to 24 h and disappearance of 4-chloro-6, 7, 8-trimethoxyquinazoline (7) was monitored by TLC using ethyl acetate and hexanes. TLC tracking to no raw material points (expansion agent: petroleum ether: ethyl acetate = 1:1, V/V), stop the reaction, after cooling, solid precipitated, filtrated, recrystallized and dried to give 6, 7, 8- trimethoxyl-4-anilinoquinazoline (Tg1-14).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Chloro-2,4-difluoroaniline, its application will become more common.

Reference:
Article; Liu, Fang; Huai, Ziyou; Xia, Guotai; Song, Liuping; Li, Sha; Xu, Yulan; Hong, Kangjun; Yao, Mingyue; Liu, Gang; Huang, Yinjiu; Bioorganic and Medicinal Chemistry Letters; vol. 28; 14; (2018); p. 2561 – 2565;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 15205-15-9, name is 2-Chloro-6-fluorobenzylamine, molecular formula is C7H7ClFN, 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. Formula: C7H7ClFN

General procedure: To an oven-dried screw-capped reaction tube equipped with a magnetic stirring bar theketone (1 eq), amine (2.8 eq), 4-nitrophenyl azide (2 eq), acetic acid (10 mol%) and 4 Amolecular sieves (50 mg) were added. The reaction mixture was dissolved in toluene(0.3M) and stirred at 100 C for 18 hours. The crude reaction mixture was then directlypurified by column chromatography (silica gel) at first with dichloromethane (DCM) aseluent to remove all 4-nitroaniline formed during the reaction followed by using a mixtureof heptane and ethyl acetate as eluent to afford the corresponding 1,2,3-triazoles asyellow oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 15205-15-9, its application will become more common.

Reference:
Article; Karypidou, Konstantina; Ribone, Sergio R.; Quevedo, Mario A.; Persoons, Leentje; Pannecouque, Christophe; Helsen, Christine; Claessens, Frank; Dehaen, Wim; Bioorganic and Medicinal Chemistry Letters; vol. 28; 21; (2018); p. 3472 – 3476;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 4863-91-6, 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. 4863-91-6 name is 3-Chloro-5-fluoroaniline, 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.

Example 4: Synthesis of Compound 33 33 Compound 33 Compound 33 [099] A flame-dried flask was charged with 2-bromonitrobenzene (50 mg, 0.25 mmol, 1 equiv) tris(dibenzylideneacetone)dipalladium (11.3 mg, 0.0012 mmol, 5 mol%), racemic 2,2′- bis(diphenylphosphino)-l, l’-binaphthyl (11.5 mg, 0.0019 mmol, 7.5 mol%), and cesium carbonate (163.1 mg, 0.50 mmol, 2 equiv). The flask was degassed and purged with nitrogen. Toluene (2.88 mL) was added, followed by 2-chloro-4-fluoroaniline (35.3 mg, 0.25 mmol, 1 equiv). The reaction was heated to 100C with a reflux condenser and stirred for 12 h. The mixture was cooled to room temperature, filtered through a pad of celite, dried over MgS04 and concentrated under reduced pressure. Purification by flash chromatography on silica gel (9: 1 hexanes:ethyl acetate) afforded the desired aniline 33 as an orange solid (58 mg, 88% yield): XH NMR (400 MHz, Acetone-d6) 9.27 (bs, 1H), 8.18 (d, J= 8.5 Hz, 1H), 7.63 (d, J = 8.6 Hz, 1H), 7.52 (d, J = 8.6 Hz, 1H), 7.28 (s, 1H), 7.17 (dt, J= 2.2 Hz, 10.4 Hz, 1H), 7.04 (m, 2H); 13C NMR (100 MHz, Acetone-d6) 164.2 (d, J = 245.7 Hz), 144.0 (d, j = 1 1.8 Hz), 140.9, 136.7, 136.6, 136.2 (d, J= 13.0 Hz), 127.2, 120.7, 1 18.9, 1 18.9, 1 12.0 (d, J= 25.4 Hz), 108.6 (d, J = 24.5 Hz);LCMS (ESI) calc’d for [Ci2H7ClFN202]”([M-H]”): m/z 265.0, found 265.1.

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

Reference:
Patent; THE BOARD OF REGENTS OF THE UNIVERSITY OF TEXAS SYSTEM; BRUICK, Richard, K.; CALDWELL, Charles, G.; FRANTZ, Doug, E.; GARDNER, Kevin, H.; MACMILLAN, John, B.; SCHEUERMANN, Thomas, H.; TAMBAR, Uttam, K.; WO2014/78479; (2014); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 886762-39-6, These common heterocyclic compound, 886762-39-6, name is 3,4-Dichloro-2-fluoroaniline, 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.

To a stirred solution of [4-chloro-7-(2,2-dimethylpropanoyloxy)quinazolin-6-yl] 2,2-dimethylpropanoate (6.6 g, 18.1 mmol) in DCE (60 mL) was added HCI, 4 M in dioxane (9 mL) followed by 3,4-dichloro-2-fluoroaniline (3.1 g, 17.2 mmol) and the resulting mixture was stirred at 70 C for 1 .5 h. The mixture was then cooled to room temperature and diluted with diethyl ether. The resulting suspension was filtered to collect the desired product (8.5 g, 92%).

The synthetic route of 886762-39-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TRILLIUM THERAPEUTICS INC.; SLASSI, Abdelmalik; DOVE, Peter; (124 pag.)WO2016/123706; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 118754-53-3, 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 118754-53-3 as follows.

Preparation of 2,6-dichloro-4-trifluoromethylbenzoic acid To a mixture of 65.2 ml of n-butyllithium (1.61M in hexane) and 100 ml of anhydrous ether was added dropwise 29.3 g of 4-bromo-3,5-dichlorobenzotrifluoride (3) in 30 ml of anhydrous ether at -78 C., followed by stirring for 20 minutes. Subsequently, 10 g of dry ice crashed into small pieces was added in small portions to the reaction mixture, followed by stirring at room temperature for 1.5 hours. Ice water was added to the reaction mixture, the mixture was thereafter extracted with ether, and the combined extract was subjected to reverse extraction with 10% aqueous sodium carbonate solution. The aqueous layer was acidified with 6N hydrochloric acid, followed by extraction with ethyl acetate, washing with brine and drying over anhydrous magnesium sulfate. Removal of the solvent under reduced pressure gave 20.4 g of the desired product in the form of white crystals (crude yield 79.1%). mp 117~118 C. 1 H-NMR (CDCl3, TMS, delta ppm): 6.21(br, s, 1H), 7.64(s,2H)

According to the analysis of related databases, 118754-53-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Otsuka Kagaku Kabushiki Kaisha; US5739083; (1998); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 14862-52-3, A common heterocyclic compound, 14862-52-3, name is 3,5-Dibromochlorobenzene, molecular formula is C6H3Br2Cl, 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 compound entitled was synthesized in accordance with the following scheme. Into a 1L four-necked glass flask equipped with a thermometer, a reflux condenser and a stirrer, 3,5-dibromochlorobenzene 20.0 g (74.0 mmol), phenylboronic acid 27.0 g (222 mmol), 2.0 mol/l sodium carbonate aqueous solution 285 ml (570 mmol), and toluene:tetrahydrofuran (1:1) solution 500 ml were added, and nitrogen was passed through the solution for 2 hours and 30 minutes. Tetrakistriphenylphosphine palladium(0) 4.28 g (3.70 mmol) was then added, which was reacted for 28 hours at 73 to 75 C with stirring followed by further addition of phenylboronic acid 4.10 g (33.6 mmol) and tetrakistriphenylphosphine palladium(0) 1.10 g (950 mumol) and reaction for 24 hours at 73 to 75 C with stirring. After completion of the reaction, the reaction mixture was cooled down to room temperature and separated with the addition of water and toluene, and after the water layer was extracted with toluene and after the organic layers were combined and washed with water, it was dried with anhydrous magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure, and the obtained concentrate was purified by silica-gel column chromatography (eluent: hexane) to obtain 3,5-diphenylchlorobenzene 16.0 g as white solid (isolation yield; 82 %).

The synthetic route of 14862-52-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ube Industries, Ltd.; EP2332907; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 53145-38-3, These common heterocyclic compound, 53145-38-3, name is 2-Chloro-6-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.

Example 1 : Synthesis, Isolation, and Use of PBA-diMe A solution of 2,6-CFA (15.2 g, 93.5 mmol) in anhydrous DME (118 mL) was prepared in a 500 mL bottle. Molecular sieves were added to remove water, and the water content was measured by Karl Fischer titration to assure water < 100 ppm (80 ppm measured). The solution was transferred to a reactor through a septum port and the septum was replaced. A nitrogen pad was started. An agitator was started and set at 270 rpm. A dewar dish under the reactor was filled half full with acetone solvent. Dry ice chunks were slowly added. When the bath solvent was cold more solvent was slowly added so the bath solvent level was above the level of the 2,6-CFA solution in the reactor. The bath was maintained at -76C during the experiment by adding dry ice chunks periodically. The 2,6-CFA solution was allowed to cool to -72C. w-BuLi in hexanes (2.5 M, 41.5 ml) was loaded into a 60 mL plastic syringe and positioned on a syringe pump. The syringe pump was started with an addition rate of 0.7 ml/min. The n-BuLi addition was complete after 64 minutes. The reaction solution was held as -72C for 57 minutes. B(OMe)3 (13. lg, 14.06 mL) was loaded into a 24 mL plastic syringe and positioned on the syringe pump. The agitator was increased to 302 rpm. With the reaction solution at -72C, the syringe pump was started with an addition rate of 0.4 mL/min. The borate addition was complete after 40 minutes. The reaction solution was left in the cold bath over night at 220 rpm agitation. A total of 153 g of the reaction solution containing PBA-diMe was collected. A GC method with an internal standard was used to quantify the amount of PBA-diMe in solution. A conversion to PBA-diMe of 98% was calculated with 2% of the original unconverted 2,6-CFA also quantified. The PBA-diMe solution was stirred at 18C in the reactor. The agitator was started and set to 294 rpm. C02 gas from a small lecture bottle was slowly bubbled into the solution through a inch (0.635 cm) glass tube over 42 minutes. The solution heated to 21 C. A total of 7.2 g (1.5 equivalents) of C02 gas was added. The mixture was very cloudy with fine white solids. The mixture (153 g) was filtered in a 7.5 cm Buchner funnel using 1 Whatman filter paper and a water aspirator. Fine white solids were removed (lithium methyl carbonate). 3.5 g of hexane was used to rinse the solids. 141 g of filtrate was collected. 3.5 g of dry white solids were collected. The PBA-diMe filtrate solution was place in a 500 mL round bottom flask on a roto-vap fitted with a water aspirator, dry ice trap, and an overhead receiver. The roto-vap was started with the bath at 25C. The vacuum ranged from 45 mmHg down to 15 mmHg and the final bath temperature was 31C. After 17 minutes 106.5 g of overhead solvent was collected and 30.1 g of bottoms remained. Analysis of the bottoms by GC gave 59.4 % by weight of PBA. The procedure resulted in 97 % recovery of PBA. Statistics shows that 2-Chloro-6-fluoroanisole is playing an increasingly important role. we look forward to future research findings about 53145-38-3. Reference:
Patent; DOW AGROSCIENCES LLC; OPPENHEIMER, Jossian; MENNING, Catherine A.; HENTON, Daniel R.; WO2013/101987; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics