Month: August 2021

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. 328-72-3, name is 3,5-Bis(trifluoromethyl)chlorobenzene, A new synthetic method of this compound is introduced below., Application In Synthesis of 3,5-Bis(trifluoromethyl)chlorobenzene

Example 13 Synthesis of Methyl 3,5-bis(trifluoromethyl)cinnamate 0.619 g (7.2 mmol) of methyl acrylate, 38.7 mg (120 mumol) of NBu4Br, 6.7 mg (30 mumol) of palladium acetate and 26.7 mg (120 mumol) of phenyldi(t-butyl)phosphine are weighed into a Schlenk vessel. 1.49 g (6 mmol) of 3,5-bis(trifluoromethyl)chlorobenzene and 1.53 ml (7.2 mmol) of dicyclohexylmethylamine and also 3.5 ml of dimethylacetamide are then added. The Schlenk vessel is placed in a heating bath at 130 C. and the contents are stirred. After 4 hours, the contents are poured into 30 ml of water and the product is extracted by shaking with t-butyl methyl ether. After drying the organic phase over MgSO4, the solvent is removed under reduced pressure and the product is isolated. Yellowish, crystalline solid, yield: 1.34 g (97% of theory).

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:
Patent; Rampf, Florian; Eckert, Markus; US2003/105353; (2003); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 51419-59-1, These common heterocyclic compound, 51419-59-1, name is p-Tolylmethanesulfonyl chloride, 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.

1.0 g of 6-amino-1-propyl-2(1H)-quinolinone and 1.2 equivalents of p-methylbenzylsulfonyl chloride were added to 20 ml of DMF, and 3 equivalents of potassium carbonate was added as an acid binding agent. The reaction was maintained at room temperature and stirred for 12-16 hours. After that, ice water was added and the mixture was extracted with ethyl acetate for three times and the organic phase was combined and dried over anhydrous sodium sulfate. The organic phase was concentrated and the crude product was subjected to silica gel column chromatography to give 1.3 g of compound 1022B with a yield of 70percent. (0326) 1HNMR (400 MHz, DMSO-d6): delta 0.95 (t, 3H), 1.62 (m, 2H), 2.27 (s, 3H), 4.18 (t, 2H), 4.42 (s, 2H), 6.60 (d, 1H), 7.12-7.17 (m, 4H), 7.40 (d, 1H), 7.45 (s, 1H), 7.55 (d, 1H), 7.83 (d, 1H) ppm; 13CNMR (100 MHz, DMSO-d6) delta 11.53, 20.99, 21.54, 43.35, 57.34, 116.08, 119.20, 121.17, 122.14, 124.01, 126.89, 129.46, 131.34, 133.02, 135.97, 138.12, 139.45, 161.12 ppm.

The synthetic route of 51419-59-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SHANGHAI INSTITUTES FOR BIOLOGICAL SCIENCES, CHINESE ACADEMY OF SCIENCES; ZHU, Jiankang; ZHANG, Yulu; CAO, Minjie; LIU, Xue; WANG, Qiuhua; US2019/84; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 202197-26-0, 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. 202197-26-0 name is 3-Chloro-4-((3-fluorobenzyl)oxy)aniline, 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.

3-Chloro-4-((3-fluorobenzyl)oxy)aniline (12.58 g, 50 mmol) was added to 100 ml of toluene and stirred well.Thereafter, 0.4 g of acetic acid (as a catalyst) was added, followed by dropwise addition of triethyl orthoformate (3.8 g, at room temperature using an addition funnel.25 mmol), after the addition of the Dean-Stark apparatus, the reaction mixture was placed in an oil bath and heated to 80 C for 1 h.The ethanol was collected by a Dean-Stark apparatus; then the temperature was raised to 110 C for 2 h, and after the reaction was completed, it was cooled to room temperature and placed in an ice bath.The solid was precipitated, filtered, and the filter cake was washed with a little toluene to give (E)-N’-(3-chloro-4-((3-chlorobenzyl)oxy)phenyl)-N-(3-Chloro-4-((3-fluorobenzyl)oxy)phenyl)carboxamidine 12.4 g, yield 93.7%. The HPLC purity was 99.14%.

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

Reference:
Patent; Yancheng Normal College; Nanjing University Of Technology Dafeng Ocean Industrial Institute; Sun Yaquan; Zong Chaoyang; Gu Huiwen; (10 pag.)CN108440420; (2018); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 139512-70-2,Some common heterocyclic compound, 139512-70-2, name is 4-Chloro-5-fluorobenzene-1,2-diamine, molecular formula is C6H6ClFN2, 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.

Intermediate compound 5 (0.2 g, 1.24 mmol) and benzil 6d (0.26 g, 1.24 mmol) were weighed and dissolved in 20 mL glacial acetic acid. This mixture was refluxed for 2.5hr. The completion of reaction was monitored by TLC. The reaction mixture was cooled and poured into crushed ice. The precipitated product was filtered off and washed with cold water. The product was then purified by column chromatography using hexane: ethyl acetate as mobile phase. The pure fractions obtained were dried and concentrated to obtain white solids of product 7d. (yield 82%, m.p. 110-112 C). 1H NMR (400 MHz, CDCl3), delta ppm, 7.3381-7.2488 (m, 6H, Ar-3,4,5-H at C-2 and C-3), 7.441-7.411 (m, 4H, Ar-2,6-H at C-2 and C-3), 7.8824 (d, J = 9.28, -H at C-5), 8.1930 (d, J = 7.6, -H at C-8). 13C NMR (400 MHz, CDCl3), delta ppm, 113.66, 113.87, 125.44, 125.66, 128.38, 129.18, 129.27, 129.78, 129.81, 130.38, 138.38, 138.53, 138.46, 140.50, 140.61, 153.73, 153.76, 154.39, 156.93, 159.46. Mass (ESI), C20H12ClFN2, M+ and [M+2]+ peaks were found at 334 and 336, respectively.

The synthetic route of 139512-70-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Patel, Saloni B.; Patel, Bhumika D.; Pannecouque, Christophe; Bhatt, Hardik G.; European Journal of Medicinal Chemistry; vol. 117; (2016); p. 230 – 240;,
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. 2106-02-7, name is 2-Chloro-4-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows., name: 2-Chloro-4-fluoroaniline

General procedure: To a well stirred solution of compound 6a or 6b (0.2 g, 1 Eq.) in absolute ethanol (10 mL), the appropriately substituted anilines(1.1 Eq) was added and the reaction mixture was refluxed for 2-3 h until TLC showed full consumption of starting materials. The excess of solvent was evaporated under reduced pressure to yield the crude solids, which were further purified by recrystallization with methanol to afford the desired title compounds (7-43).

According to the analysis of related databases, 2106-02-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Cherukupalli, Srinivasulu; Chandrasekaran, Balakumar; Kry?tof, Vladimir; Aleti, Rajeshwar Reddy; Sayyad, Nisar; Merugu, Srinivas Reddy; Kushwaha, Narva Deshwar; Karpoormath, Rajshekhar; Bioorganic Chemistry; vol. 79; (2018); p. 46 – 59;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 19230-27-4, The chemical industry reduces the impact on the environment during synthesis 19230-27-4, name is 1,3-Dibromo-2-chlorobenzene, I believe this compound will play a more active role in future production and life.

A mixture of 9a (340 mg, 2.47 mmol, 1.0 eq), 9b (1.0 g, 3.70 mmol, 1.5 eq), potassium carbonate (1.03 g, 7.41 mmol, 3.0 eq). Cuprous iodide (141.0 mg, 0.74 mmol, 0.3 eq), and L-proline (85.0 mg, 0.74 mmol, 0.3 eq) in 2-pentanol (30.0 mL) was stirred at 140 C overnight under argon atmosphere, then cooled to room temperature. Water (50.0 mL) was added. The mixture was filtered through celite. The filtrate was acidified to pf i 2 with 2 N HC1, then water (50.0 mL) was added. The resulting mixture was extracted with EtOAc (50.0 ml, x 3) The combined organic layers were washed with brine (20.0 mL x 5), dried over anhydrous NaaSOr and filtered. The filtrate was concentrated in vacuo to afford 9c (crude, 600 mg, 74.5%). LC/MS: 326.0 j M S | .

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, 1,3-Dibromo-2-chlorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SILICON SWAT, INC.; CHAMBERLAIN, Brian T.; RICE, James M.; JERNIGAN, Finith E., III; SHERMAN, Woody; KULKARNI, Meghana M.; SHECHTER, Sharon; ALLEN, Bryce K.; TAN, Dazhi; MARINO, Kristen A.; LIN, Zhixiong; (292 pag.)WO2019/100061; (2019); 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. 367-22-6, name is 4-Chloro-3-fluoroaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 367-22-6

To 4-chloro-3-fluoroaniline (25g, 0.17 mmol) in 250 mL of H20 was added NaHC03 (21.6g, 0.25 mmol). After cooling to 0 C, iodine (43.5 g, 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 ( a2S04). Purification by silica gel chromatography gave 47 g of Intermediate 5A.MS (ESI) m/z: 145.2 (M+H)+.

The synthetic route of 367-22-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; ORWAT, Michael J.; PINTO, Donald J.P.; SMITH II, Leon M.; SRIVASTAVA, Shefali; CORTE, James R.; WO2013/55984; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 19393-92-1,Some common heterocyclic compound, 19393-92-1, name is 2-Bromo-1,3-dichlorobenzene, molecular formula is C6H3BrCl2, 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 148 (7bR,11aS)-N-(2,6-dichlorophenyl)-1,2,7b,8,9,10,11,11a-octahydro-4H-pyrido[4,3-b][1,4]thiazepino[6,5,4-hi]indol-6-amine An oven-dried three-necked round bottom flask was fitted with a septa, condenser, and a stopper. The flask was charged with tert-butyl (7bR,11aS)-6-amino-1,2,7b,10,11,11a-hexahydro-4H-pyrido[4,3-b][1,4]thiazepino[6,5,4-hi]indole-9(8H)-carboxylate from EXAMPLE 33, Part B (107 mg, 0.297 mmol), 2,6-dichlorobromobenzene (56 mg, 0.25 mmol), NaOt-Bu (71 mg, 0.74 mmol), and anhydrous toluene (6 mL). The solution was purged with argon at 80° C. for 25 min then cooled to room temperature. While maintaining a blanket of argon, Pd2(dba)3 (5 mg, 6 mumol), and BINAP (7 mg, 12 mumol) were added quickly. The resulting mixture was heated to 80° C. for 20 h under argon. After cooling to room temperature, the dark solution was diluted with ethyl ether (10 mL) and filtered through a pad of silica, washing with ether. The resulting solution was concentrated and the residue was chromatographed (10-12percent ethyl acetate in hexanes gradient) yielding an N-BOC intermediate (90 mg, 72percent) as a yellow foam: 1H NMR (300 MHz, CDCl3) delta 1.40 (s, 9H), 1.71-1.92 (m, 2H), 2.79-3.13 (m, 3H), 3.15-3.96 (m, 9H), 5.71 (s, 1H), 6.29-6.50 (m, 2H), 6.91-7.00 (s, 1H), 7.32 (d, 2H, J=8 Hz). This intermediate (90 mg, 0.18 mmol) was dissolved in dichloromethane (8 mL) and chilled in an ice bath. Trifluoroacetic acid (2 mL) was then added and the solution was stirred at room temperature for 2 h. The solution was made basic with 3 N NaOH, and extracted with dichloromethane. The organic layers were combined, dried over NaSO4 and concentrated to a yellow oil. An off-white solid was obtained upon trituration with ethyl acetate/hexanes yielding 58 mg (81percent) of the title compound of EXAMPLE 148. 1H NMR (300 MHz, CDCl3) delta 1.72-1.85 (m, 2H), 2.51-2.65 (m, 1H), 2.76-3.09 (m, 6H), 3.10-3.21 (m, 1H), 3.36-3.42 (m, 1H), 3.47-3.79 (m, 4H), 5.71 (s, 1H), 6.34 (s, 1H), 6.42 (s, 1H), 6.95 (t, 1H, J=8 Hz), 7.32 (d, 2H, J=8 Hz). LRMS (ES)+: 406 (M+H)+.

The synthetic route of 19393-92-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Robichaud, Albert J.; Fevig, John M.; Mitchell, Ian S.; Lee, Taekyu; Chen, Wenting; Cacciola, Joseph; US2004/186094; (2004); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 210532-25-5, These common heterocyclic compound, 210532-25-5, name is 3,5-Difluorobenzene-1-sulfonyl chloride, 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: Preparation of target compounds 3a-k: Intermediate 2 (0.1 g)and arylsulfonyl chloride (1 equiv) were dissolved in 3 mL dry pyridineat 0 C, and the reaction mixture was stirred overnight atroom temperature. The reaction was quenched by adding waterand acidifying the solution with 3 mL concentrated HCl. The productwas filtered and washed with water, or was extracted withethyl acetate and dried over Na2SO4, and the solvent was evaporated.If needed, further purification was achieved by recrystallizationfrom absolute methanol, affording target compounds 3a-k.

The synthetic route of 210532-25-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Huang, Boshi; Wang, Xueshun; Liu, Xinhao; Chen, Zihui; Li, Wanzhuo; Sun, Songkai; Liu, Huiqing; Daelemans, Dirk; De Clercq, Erik; Pannecouque, Christophe; Zhan, Peng; Liu, Xinyong; Bioorganic and Medicinal Chemistry; vol. 25; 16; (2017); p. 4397 – 4406;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

1940-29-0, name is 4-Bromo-3,5-dichloroaniline, 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. Computed Properties of C6H4BrCl2N

*5*.(4-Bromo-3,5-dichloro-phenyl)-l-(4-methoxy-benzyl)-N*3*,N*3*-dimethyl-lH- [l,2,4]triazole-3,5-diamine In a 25 mL round bottle, 5-bromo-l-(4-methoxybenzyl)-N,N-dimethyl-lH-l,2,4-triazol-3-amine (lg, 3.21 mmol, Eq: 1.00) was combined with DMF (18.4 ml) to give a colorless solution. 4- bromo-3,5-dichloroaniline (774 mg, 3.21 mmol, Eq: 1.00) and sodium 2-methylpropan-2-olate (618 mg, 6.43 mmol, Eq: 2.00) were added. The reaction was degassed by nitrogen for 5 min. The resulting solution was heated to 85 C overnight under nitrogen. The reaction mixture was cooled and diluted with 20 mL H20, added EtOAc (30×2 mL) to extract the product, dried the organic layer over anhydrous Na2S04, concentrate the solution, purify the compound by column (Hexanes/EtOAc = 70/30) to afford the compound 40mg (3%). MH+ 472.0

The synthetic route of 1940-29-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; DING, Qingjie; JIANG, Nan; WEIKERT, Robert James; WO2014/135472; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics