Author: Jessica.F

Electric Literature of 5414-19-7,Some common heterocyclic compound, 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane, molecular formula is C4H8Br2O, 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 solution of ethylsulfone acid 833a (2.06 g, 8.79 mmol) in anhydrous THF at-78C under N2 was added LiHMDS solution (19.3 mL, 1.0 Min THF). The mixture was stirred at-78C for 30 min before it was allowed to warmed to 0C along with a cold acetone bath. It was then re-cooled to-78C and to it was added 2-bromoethyl ether (1.8 mL, 13. 2 mmol). After stirred at- 78C for 30 min, the mixture was warmed to rt and stirred for 2 h. It was again re-cooled to-78C and to it was added LiHMDS solution (10.6 mL, 10.6 mmol). After stirred at-78C for 30 min, the mixture was warmed to rt and stirred for 3 h before it was quenched with 1 N aqueous HCI solution until the pH is about 1-2. The solution was extracted with CH2CI2 (2×450 mL). Combined organic solution was dried (MgS04), filtered and concentrated. The crude product was dissolved in 1 N NaOH solution (300 mL) and extracted with EtOAc (100 mL). After layers were separated, the organic solution was washed with 1 N NaOH (2×150 mL). The combined aqueous solution was acidified to pH-1 using 6 N HCI solution. It was extracted with EtOAc (3 x 300 mL). The organic solutions were combined, dried (MgSO4), filtered and concentrated to give 2.3 g product (833b; 7.56 mmol, 89%).

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-2-(2-bromoethoxy)ethane, its application will become more common.

Reference:
Patent; SCHERING CORPORATION; WO2005/87731; (2005); A1;,
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Application of 2398-37-0, A common heterocyclic compound, 2398-37-0, name is 1-Bromo-3-methoxybenzene, molecular formula is C7H7BrO, 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: To a reaction tube charged with NBS (1.5 equiv, 0.3 mmol), catalyst (10 mol%, 0.02 mmol) and CH3CN (1.0 mL),was added para-chloroanisole 1a (0.2 mmol). After being stirred at room temperature for 12 h in dark, the reaction was quenched by saturated aq. solution of Na2S2O3 (2 mL). The resulting mixture was extracted by ethyl acetate (3 5 mL). The combined organic extracts were washed by brine (10 mL), dried over Na2SO4 and filtered through a pad of Celite. The filtrate was concentrated under reduced pressure and the residuewas purified by flash chromatography on a silica gel column with petroleum ether/dichloromethane (5:1) as the eluent to give 4.3.1. 2-Bromo-4-chloroanisole (2a)

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:
Article; Pramanick, Pranab Kumar; Hou, Zhen-Lin; Yao, Bo; Tetrahedron; vol. 73; 50; (2017); p. 7105 – 7114;,
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Related Products of 627527-23-5, 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. 627527-23-5, name is 1-Bromo-3-methoxy-5-(trifluoromethyl)benzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 2: Preparation of 8-[3-methoxy-5-(trifluoromethyl)phenyl]-1,4-dioxa-8- azaspiro[4.5]decane To a mixture of 1-bromo-3-methoxy-5-(trifluoromethyl)benzene (500 mg, 1.96 mmol), 1,4-dioxa-8-azaspiro[4.5]decane (281 mg, 1.96 mmol) and sodium tert-butoxide (377 mg, 3.92 mmol) in dioxane (10 mL) was added Pd2(dba)3 (71.8 mg, 78.4 mumol) and Ruphos (18.3 mg, 39.2 mumol) under N2. The resulting mixture was then heated with stirring at 100oC overnight. After being cooled down to rt, the resulting mixture was diluted with H2O (10 mL) and extracted with EA (30 mL) for three times. The organic layers were combined, dried over anhydrous Na2SO4 and concentrated in vacuo to give crude 8-(3-methoxy-5-(trifluoromethyl)phenyl)-1,4- dioxa-8-azaspiro[4.5]decane (650 mg) which was used in the next step directly without an further purification.

The synthetic route of 1-Bromo-3-methoxy-5-(trifluoromethyl)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; HAN, Xingchun; JIANG, Min; WANG, Jianhua; WANG, Min; WANG, Yongguang; YANG, Song; (319 pag.)WO2016/177655; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 18800-30-1, name is 1-Bromo-4-(2-bromoethoxy)benzene, belongs to ethers-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 18800-30-1, Recommanded Product: 1-Bromo-4-(2-bromoethoxy)benzene

KOr-Bu (14.0 g, 125 mmol) was added in portions over 10 min to l-bromo-4- (2-bromoethoxy)benzene (19.9 g, 100 mmol see step (a) above) in THF (120 mL) at 0 0C. After 16 h at rt, water (400 mL) was added and the mixture was extracted with petroleum ether (4 x 100 mL). The combined extracts were washed with brine, dried (Na2SO4), concentrated and distilled under vacuum to yield the subtitle compound (11.5 g, 58%).

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-4-(2-bromoethoxy)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BIOLIPOX AB; WO2006/77364; (2006); A1;,
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Related Products of 5905-69-1, 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 5905-69-1 as follows.

A. 2-(4-(difluoromethoxy)phenyl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolaneA mixture of commercially available l-bromo-4-(difluoromethoxy)benzene (1 g, 4.48 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(l,3,2-dioxaborolane) (1.2g, 4.71 mmol), potassium acetate (1.3 g, 13.4 mmol), and PdCl2(dppf)-CH2Cl2 Adduct (0.18 g, 0.22 mmol) in DMF (15 mL) was stirred under nitrogen at 90 0C for 1 hour. Diluted with DCM, washed with water, sat. NaHCC^, brine, dried (MgSC^), and concentrated.The crude was purified using ISCO flash chromatography (silica gel/ hexanes/ethyl acetate 100:0 to 50:50 gradient) to afford the desired product 2-(4- (difluoromethoxy)phenyl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolane 13A (1.12 g, 3.32 mmol, 74.0 % yield) as a brown oil.

According to the analysis of related databases, 5905-69-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; AHMAD, Saleem; WASHBURN, William, N.; HERNANDEZ, Andres, S.; ROBL, Jeffrey, A.; NGU, Khehyong; WANG, Zhenghua; WO2010/104830; (2010); A1;,
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Reference of 39538-68-6, 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. 39538-68-6, name is 2-Methoxy-4-methylaniline, This compound has unique chemical properties. The synthetic route is as follows.

A solution of 2-methoxy-4-methylaniline (18, 10.9 mmol), bis-(2-chloroethyl)amine hydrochloride (12.0 mmol), potassium carbonate (15.2 mmol) in 1-butanol (5 mL) was refluxed under nitrogen overnight. The hot reaction mixture was filtered and the filtrate was concentrated under vacuum. The resulting residue was triturated with acetone and filtered to give 19 as an off-white powder (14% yield), mp 212-213 C (dec); 1H NMR (free base, CDCl3) delta 9.14 (s, 1H), 6.68-6.82 (m, 3H), 3.77 (s, 3H), 3.11-3.19 (m, 8H), 2.25 (s, 3H).

The chemical industry reduces the impact on the environment during synthesis 2-Methoxy-4-methylaniline. I believe this compound will play a more active role in future production and life.

Reference:
Article; Vangveravong, Suwanna; Zhang, Zhanbin; Taylor, Michelle; Bearden, Melissa; Xu, Jinbin; Cui, Jinquan; Wang, Wei; Luedtke, Robert R.; MacH, Robert H.; Bioorganic and Medicinal Chemistry; vol. 19; 11; (2011); p. 3502 – 3511;,
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Related Products of 2752-17-2, 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. 2752-17-2, name is 2,2′-Oxydiethanamine, This compound has unique chemical properties. The synthetic route is as follows.

1-Hydroxypyrene-2-carbaldehyde 3 (100 mg, 0.41 mmol) wasdissolved in CH2Cl2 and 2,2′-oxybis (ethylamine) (0.02 mL,0.20 mmol) was added to the reaction mixture. The reactionmixture was stirred at RT for 12 h. The precipitate formed wasfiltered and washed with cold CH2Cl2 to give 2 as a yellow solid(176 mg, 76.6%). m.p. 200 C. 1H NMR (CDCl3, 250 MHz): delta 14.53(s, OH), 8.61 (s, 2H), 8.32 (d, J 9.10 Hz, 2H), 7.99-7.80 (m, 8H), 7.54(s, 2H), 7.35 (d, J 8.98 Hz, 2H), 3.91 (s, 8H). 13C NMR (CDCl3,62.5 MHz): delta 167.16, 156.66, 132.52, 132.18, 127.00, 127.12, 126.88,126.81, 126.66, 125.97, 124.77, 124.20, 123.90, 122.96, 121.49, 119.52,115.34, 69.91, 58.44, 30.92. HRMS (FAB) calcd for C38H29N2O3[M + H]+ 561.2100; found 561.2178.

The chemical industry reduces the impact on the environment during synthesis 2,2′-Oxydiethanamine. I believe this compound will play a more active role in future production and life.

Reference:
Article; Hu, Ying; Liu, Yifan; Kim, Gyoungmi; Jun, Eun Jin; Swamy; Kim, Youngmee; Kim, Sung-Jin; Yoon, Juyoung; Dyes and Pigments; vol. 113; (2015); p. 372 – 377;,
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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. 20781-20-8, name is (2,4-Dimethoxyphenyl)methanamine, A new synthetic method of this compound is introduced below., Quality Control of (2,4-Dimethoxyphenyl)methanamine

Into a vial was added the 4-bromo-2-fluoro-N-thiazol-2-yl-benzenesulfonamide (2.60 g, 0.00771 mol), sodium tert-butoxide (1.78 g, 0.0185 mol), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (0.27 g, 0.00046 mol), tris(dibenzylideneacetone)dipalladium(0) (0.14 g, 0.00015 mol) and 1,4-dioxane (24.1 mL, 0.308 mol). Argon was bubbled for 15 minutes. 2,4-Dimethoxybenzylamine (1.40 mL, 0.00925 mol) was added and the reaction mixture was heated at 100 C. overnight. The reaction mixture was cooled to room temperature then filtered over Celite. The filtrate was concentrated to give the crude product that was purified via automated flash chromatography (silica gel, 50% EtOAc in hexanes to 100% EtOAc) to give the product as a yellow solid (2.59 g, 79.3%)

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; Icagen; US2009/23740; (2009); A1;,
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Some common heterocyclic compound, 645-36-3, name is 2,2-Diethoxyethanamine, molecular formula is C6H15NO2, 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. HPLC of Formula: C6H15NO2

[00114] To a glass reactor was charged 3,5-dichlorobenzaldehyde. Absolute ethanol was added to the batch slowly (this addition is mildly exothermic) and agitation started. 2,2- Diethoxyethylamine (1.03 equiv) was slowly added to the batch, keeping the batch temperature at 20-78 C. The batch was then heated to 76-78 C for 2 h. GC-MS analysis indicated reactioncompletion (starting material < 1%). The batch was cooled to ambient temperature for work-up. The batch was concentrated in vacuo to a residue and azeotroped with heptanes (x2). The residue was cooled and held at 0-5 C for 12 h to form a suspension. The solids were collected by filtration and the cake was washed with cold (0-5 C) heptanes, and dried under hot nitrogen (45-5 0 C) to afford Compound 2? as a white solid (94% yield). These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 645-36-3, its application will become more common. Reference:
Patent; SARCODE BIOSCIENCE INC.; ZELLER, James, Robert; VENKATRAMAN, Sripathy; BROT, Elisabeth, C.A.; IYER, Subashree; HALL, Michael; WO2014/18748; (2014); A1;,
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Synthetic Route of 2688-84-8, 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. 2688-84-8, name is 2-Phenoxyaniline, This compound has unique chemical properties. The synthetic route is as follows.

5.58.1 3-(2-Phenoxyphenylamino)phthalic acid dimethyl ester A mixture of 3-iodophthalic acid dimethyl ester (1.0 g, 3.1 mmol), 2-phenoxyaniline (0.57 g, 3.1 mmol), Pd2(dba)3 (0.13 g, 0.14 mmol), rac-BINAP (0.058 g, 0.093 mmol), and cesium carbonate (1.4 g, 4.3 mmol), in 6 mL toluene was heated to reflux under nitrogen for 24 hours. The reaction mixture was cooled, diluted with CH2Cl2 (10 mL), and filtered through Celite, and the filter was washed with additional CH2Cl2 (30 mL). The filtrate was evaporated, and the residue was chromatographed using a hexanes-ethyl acetate gradient, eluting 0.86 g of the product at 80:20 hexanes-ethyl acetate, in 73% yield: 1H NMR (CDCl3) delta 3.75 (s, 3H), 3.86 (s, 3H), 6.93-7.03 (m, 4H), 7.06-7.12 (m, 2H), 7.17 (dd, J=7.3 Hz, J=1.0 Hz, 1H), 7.29-7.38 (m, 4H), 7.46 (d, J=8.4 Hz, 1H), 7.89 (s, 1H).

The chemical industry reduces the impact on the environment during synthesis 2-Phenoxyaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Muller, George W.; Chen, Roger Shen-Chu; Man, Hon-Wah; Ruchelman, Alexander L.; US2007/49618; (2007); A1;,
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