Author: Jessica.F

Related Products of 468075-00-5, 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. 468075-00-5, name is 2-Bromo-1-chloro-4-(trifluoromethoxy)benzene, This compound has unique chemical properties. The synthetic route is as follows.

A suspension of ethyl 2-(3-(2-chloro-5-(trifluoromethoxy)phenyl)-8-methyl-3-azaspiro[5.5]undecan-9-yl)acetate (140 mg, 0.553 mmol), cesium carbonate (540 mg, 1.66 mmol), 2-bromo-1-chloro-4-(trifluoromethoxy)benzene (0.175 ml, 1.105 mmol) and (RuPhos)palladium(II) phenethylamine chloride (40.3 mg, 0.055 mmol) in 1,4-dioxane (3 ml) in amicrowave reaction vial was bubbled with nitrogen. The vial was sealed and the mixture was stirred overnight in an oil bath kept at 100C. The mixture was diluted with aq. NH4Cl solution and extracted 3 times with ethyl acetate. The combined organic layer was washed with brine, dried over MgSO4, filtered and evaporated to dryness. The crude product was purified by chromatography eluting with 0-10%-20% ethyl acetate-hex to give ethyl 2-(3 -(2-chloro-5-(trifluoromethoxy)phenyl)-8-methyl-3-azaspiro[5.5]undecan-9-yl)acetate. LCMS m/z 448.13 [M+H]+.

The chemical industry reduces the impact on the environment during synthesis 2-Bromo-1-chloro-4-(trifluoromethoxy)benzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK SHARP & DOHME CORP.; CHELLIAH, Mariappan; CHU, Hong Dong; COX, Jason, M.; DEBENHAM, John, S; EAGEN, Keith; LAN, Ping; LONDON, Clare; PLOTKIN, Michael, A.; SHAH, Unmesh; SINZ, Christopher Joseph; SUN, Zhongxiang; VACCARO, Henry, M.; VENKATRAMAN, Skikanth; WO2014/59232; (2014); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 33863-76-2,Some common heterocyclic compound, 33863-76-2, name is 1-Bromo-3-chloro-5-fluorobenzene, molecular formula is C6H3BrClF, 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.

Reference 7; Synthesis of 2-(3-bromo-5-chlorophenyl)propanoic acid Step 1A heavy- wall flask was charged with sodium hydride (9.5 g, 239 mmol) (60% oil dispersion) in NMP (75 ml) under a positive nitrogen flow. Ethyl 2-cyanoacetate (27 g, 239 mmol) was added in a dropwise manner. The reaction mixture was stirred until no more bubbling was observed. l-Bromo-3-chloro-5-fluorobenzene (10.00 g, 48 mmol) was added to the reaction mixture. The flask was capped and the reaction mixture was heated to 115 0C. After 15 hours, the reaction mixture was cooled down and diluted with water. The pH of the reaction mixture was adjusted to 3 with 2N HCl and extracted with ether. The organics were combined and washed with an aqueous saturated solution of sodium bicarbonate, then with water and then brine. The organic layer was then dried with sodium sulfate and purified by column chromatography on silica gel using a gradient of 5 to 40 % EtOAc in hexanes to give ethyl 2-(3-bromo-5-chlorophenyl)-2-cyanoacetate (10.00 g, 69% yield) as a white semi solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-3-chloro-5-fluorobenzene, its application will become more common.

Reference:
Patent; AMGEN INC.; WO2009/75874; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 14752-66-0, 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. 14752-66-0 name is Sodium 4-chlorobenzenesulfinate, 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.

0.3 mmol of 1H-indol-2-yldiphenylmethanol (the compound corresponding to the number (1), 0.0897 g) was weighed. 0.9 mmol of sodium 4-chlorobenzenesulfinate (the corresponding compound of No. (16), 0.1787 g) and 0.6 mmol of silver nitrate (0.1019 g) in a 20 mL schlenk reaction tube. Add 2 mL of absolute ethanol as a solvent, protect with argon gas, and stir the reaction at 80 C for 12 hours; After the reaction is completed, column chromatography separation (column chromatography separation conditions: The stationary phase was 200-300 mesh silica gel, the mobile phase was ethyl acetate (A) and petroleum ether (B), and the mobile phase change procedure (A:B) was 1:5) to obtain 0.1440 g of the reaction product. According to the characterization data, the obtained reaction product is pure 3-(4-chlorobenzenesulfonyl)-2-((4-(4-chlorobenzenesulfonyl)phenyl)(phenyl)methyl)-1H-indole (purity > 95) %); Calculated for product yield, the result was 76%.

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:
Patent; Soochow University (Suzhou); Xu Xiaoping; Ji Shunjun; Zhou Yu; (11 pag.)CN108276324; (2018); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 363-51-9,Some common heterocyclic compound, 363-51-9, name is 2-Chloro-6-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 2-chloro-6-fluoroaniline (2.23 g, 15.32 mmol) in propionic acid (7.66 ml) was treated with propionic anhydride (2.369 ml, 18.38 mmol), and the reaction mixture was stirred at 90 C. for 1 h. After cooling to r.t., water was added and the solid precipitate was collected by filtration, washed with water, and air dried. The crude product obtained was used directly in the next step without further purification. LCMS calculated for C9H10ClFNO (M+H)+: m/z=202.0; Found 202.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Chloro-6-fluoroaniline, its application will become more common.

Reference:
Patent; Incyte Corporation; Hummel, Joshua; Vechorkin, Oleg; Sokolsky, Alexander; Ye, Qinda; Liu, Kai; Yao, Wenqing; (60 pag.)US2020/48241; (2020); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 918538-05-3,Some common heterocyclic compound, 918538-05-3, name is 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine, molecular formula is C6H3Cl2N3, 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 2,4-dichloropyrrolo[1,2-f][1,2,4]triazine (150 mg, 0.8 mmol), 2-oxa-6-azaspiro[3.3]heptane (103mg, 1.04 mmol) and K2C03 (221 mg, 1.6 mmol) in DMF (4.5 mL) was stirred at room temperature for 2h. TLC showed the starting material was completely consumed and DCM (10 mL) was added to the mixture, and the mixture was washed with water (5 mL) and brine. The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo to give compound 35(160 mg, 8 1%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine, its application will become more common.

Reference:
Patent; SUZHOU KINTOR PHARMACEUTICALS, INC.; GUO, Chuangxin; TONG, Youzhi; (160 pag.)WO2017/219800; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 13526-66-4, name is 3-Bromo-6-chloroimidazo[1,2-b]pyridazine, molecular formula is C6H3BrClN3, 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 3-Bromo-6-chloroimidazo[1,2-b]pyridazine

13.9 g (59.8 mmol) 3-bromo-6-chloro-imidazo[1 ,2-b]pyridazine were suspended in 508 mL 1 ,4-dioxane. 10.1 g (62.8 mmol) 2-benzofuranylboronic acid, 2.76 g (2.29 mmol) tetrakis(tn’phenylphosphino)palladium-(0) and 90 mL (180 mmol) of a 2M aqueous sodium carbonate solution were added. The obtained mixture was heated to 100C for 24 h. 400 mL of a saturated aqueous ammonium chloride solution were added. The obtained mixture was extracted with ethyl acetate. The combined organic layers were washed with brine and dried over magnesium sulfate. After evaporation of the solvent, the obtained solid material was digested in 40 mL of a mixture of dichloromethane and methanol (8:2), filtered off and dried in vacuo to yield 5.42 g (44%) of the title compound as solid material. 1H-NMR (300 MHz, DMSO-d6): delta [ppm]= 7.23 – 7.40 (2H), 7.51 (1 H), 7.59 – 7.67 (2H), 7.77 (1 H), 8.33 – 8.40 (2H). LCMS (Method 1 ): Rt = 1.35 min; MS (ESIpos) m/z = 270 [M+H]

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 13526-66-4, its application will become more common.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; EIS, Knut; PUeHLER, Florian; ZORN, Ludwig; SCHULZE, Volker; SUeLZLE, Detlev; LIENAU, Philip; HAeGEBARTH, Andrea; PETERSEN, Kirstin; BOeMER, Ulf; WO2013/144189; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

6579-54-0, name is 2,6-Dichlorobenzenesulfonyl chloride, 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. Formula: C6H3Cl3O2S

C. 3-(2,6-dichlorophenylsulfonylamino)-4-(2-pyridyl)-5-(3-(4-fluorophenoxy)benzylthio)-(1H)-pyrazole 3-Amino-4-(2-pyridyl)-5-(3-(4-fluorophenoxy)benzylthio)-(1H)-pyrazole (0.39 g, 0.99 mmol) was dissolved in 5 ml of pyridine. Commercial 2,6-dichlorobenzenesulfonyl chloride (0.26 g, 1.04 mmol) was added and the red solution was stirred overnight at room temperature. The reaction mixture was poured into 50 ml of water and was extracted twice with 100 ml portions of ethyl acetate. The organic layers were washed with water and brine, combined, dried over MgSO4and concentrated. The crude product was slurried in cold ethyl acetate and the solid was filtered off and washed with small portions of cold ethyl acetate and cold diethyl ether and dried under vacuum to afford 0.32 g (53% yield) of the final compound. FD-MS: (M+)600 mp. 164-5C

The synthetic route of 6579-54-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; EP846687; (1998); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 1435-44-5,Some common heterocyclic compound, 1435-44-5, name is 1-Chloro-2,4-difluorobenzene, molecular formula is C6H3ClF2, 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 81 3-(2,4-Difluorophenylamino)-8-nitro-6H-dibenzo[b,e]oxepin-11-one (7) In accordance with general method Z, 0.50 g (1.85 mmol) of (6), 0.28 g (1.89 mmol) of 1-chloro-2,4-difluorobenzene, 2 spatula tips of Pd(OAc)2, 0.09 g of 2-(dicyclohexylphosphino)-2′,4′,6′-triisopropylbiphenyl (phosphine ligand), 0.50 g of KOt-Bu, 1.5 ml of t-BuOH are weighed out and dissolved in 10 ml of toluene (anhydrous). The mixture is refluxed at 100 C. under an argon atmosphere for 4 h. The crude product is purified by chromatography over silica gel with MC/EtOH (98/2). Yield: 0.05 g (7.0%); melting point: 210-214 C. C20H12F2N2O4 (Mr=382.33); LC 8.97 min 1H-NMR (DMSO-d6) delta in ppm: 8.84 (s, 1H, aryl H), 8.48 (d, 1H, J=2.01 Hz, aryl H), 8.30 (m, 1H, aryl H), 8.01 (dd, 2H, J1=2.70 Hz, J2=3.25 Hz, aryl H), 7.47-7.33 (m, 2H, aryl H), 7.15-7.04 (m, 2H, aryl H), 6.63 (d, 1H, J=10.0 Hz, aryl H), 6.24 (s, 1H, aryl H), 5.34 (s, 2H, -CH2-O) 13C-NMR (DMSO-d6) in ppm: 186.11 (C11), 163.30 (C4a), not detected (C4′, C2′), 152.89 (C8), 149.52 (C3), 145.34 (C6a), 137.76 (C10a), 133.85 (C1), 131.01 (C10), 127.38 (C1′, J=9.85 Hz), 124.23 (C6′, J=14.23 Hz), 116.52 (C7), 112.57 (C5′, J=3.52 Hz), 110.35 (C2), 105.45 (C3′, J=24.29 Hz), 101.93 (C4), 72.03 (C6) IR (ATR) (cm-1): 2849, 1643, 1608, 1531, 1297, 1249, 1150, 740 MS (ESI) 381.1 [M-H]-. General Method ZThe stated amounts of 3-amino-8-nitro-6H-dibenzo[b,e]oxepin-11-one, phosphine ligand, KOt-Bu, tert-butanol, haloaromatic, Pd(OAc)2 are weighed into a dry 100 ml three-necked flask with a reflux condenser, bubble counter and thermometer. The mixture is suspended in toluene (anhydrous) under an argon atmosphere and the suspension is heated to 110 C. and refluxed for 2 h. Hydrolysis with ice-water and repeated extraction with EtOAc are carried out. The combined organic phases are filtered and then concentrated in vacuo. The residue is purified by chromatography.

The synthetic route of 1435-44-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Laufer, Stefan; Albrecht, Wolfgang; US2012/115862; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 461432-23-5, name is 4-Bromo-1-chloro-2-(4-ethoxybenzyl)benzene, 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 461432-23-5, HPLC of Formula: C15H14BrClO

Step 6: (3R, 4S, 5R, 6R) -3, 4, 5-tris (benzyloxy) -6- ( ( (tert-butyldimethylsilyl) oxy) methyl) -2- (4-chloro-3- (4-ethoxybenzyl) phenyl) tetrahydro-2H-pyran-2-ol (5f) To a solution of 4-bromo-1-chloro-2- (4-ethoxybenzyl) benzene (619 mg, 1.91 mmol) in anhydrous PhMe /THF (2:1, 12 mL) was added n-BuLi (2.4M in hexane, 0.8 mL, 1.91 mmol) dropwised at -78under nitrogen. The mixture was stirred at -78for 1 h. A mixture of compound 5e (978 mg, 1.74 mmol) in anhydrous PhMe /THF (2:1, 12 mL) was added dropwise and stirred -78for another 1 h. Then the mixture was increased from -78to -25 , and to the mixture was dropwisely added saturated NH4Cl solution (20mL) and extracted with DCM (3×15 mL) . The organic extracts were dried over MgSO4, and concentrated to produce a residue, which was purified by chromatography (200300 mesh silica gel, eluted with EtOAc/PE 1:3-1:1) to give compound 5f as a pale oil (mainly beta-epimer, 760 mg, 54) LC-MS (ESI) : 826.34 [M+NH4]+.

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, 4-Bromo-1-chloro-2-(4-ethoxybenzyl)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NATIONAL INSTITUTE OF BIOLOGICAL SCIENCES, BEIJING; ZHANG, Zhiyuan; HUANG, Shaoqiang; ZHANG, Zhaolan; SU, Yaning; REN, Yan; (73 pag.)WO2016/41470; (2016); A1;,
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. 627531-47-9, name is 4-Bromo-3-chloro-2-methylaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 627531-47-9

Concentrated HCl was added to a solution of 4-bromo-3-chloro-2-methyl-phenylamine (4.98 g, 22.60 mmol) in EtOH. NaNO2 (3.00 g, 43.50 mmol) was added and the resulting mixture was heated to 70 C. for 2 hours. Ethanol was distilled off and the residue was purified by column chromatography using hexanes as the eluant to afford the title compound. Spectroscopic data: 1H NMR (300 MHz, CDCl3) delta 2.43 (s, 3H), 7.01 (t, J=7.91 Hz, 1H), 7.18 (d, J=7.62 Hz, 1H), 7.47 (d, J=7.91 Hz, 1H).

The synthetic route of 627531-47-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Allerghan, Inc.; US2008/194650; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics