Month: January 2021

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 129316-09-2 as follows. category: bromides-buliding-blocks

Step 1 : Ethyl 5-(3-bromo-5-(teff-butyl)phenyl)-1-(cvclohexylmethyl)-2-iTiethyl-1 -/-pyrrole-3- carboxylate (12a) To a solution of compound P18a (643 mg, 1.71 mmol ) in 1 ,4-dioxane/H20 (3 mlJ0.8 ml_) 1 ,3-dibromo-5-(tert-butyl)benzene (595 mg, 2.05 mmol), Cs2C03 (1.11 g, 3.42 mmol) and Pd(PPh3)4 (66 mg, 0.17 mmol) were added under N2. The mixture was stirred under microwave at about 110C for 2.5 h. Removal of the solvents and purification by prep. TLC (PE/EA = 20/1) yielded compound 12a (275 mg, 35%) as yellow solid.

According to the analysis of related databases, 129316-09-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PHENEX PHARMACEUTICALS AG; STEENECK, Christoph; KINZEL, Olaf; GEGE, Christian; KLEYMANN, Gerald; HOFFMANN, Thomas; WO2013/79223; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 53078-85-6, These common heterocyclic compound, 53078-85-6, name is 2-Bromo-5-methylaniline, 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.

Aniline 1: Step 1: A mixture of 2-bromo-5-methylaniline (220 mg, 1 mmol) and vinylboronic acid pinacol ester (185 mg, 1.2 mmol) in Dioxane/Water (4: 1, Volume: 2.5 ml) was treated with potassium carbonate (276 mg, 2 mmol) and Pd(Ph3P)4(12 mg, 0.01 mmol). The mixture was heated at 100 C for 16 h and cooled to rt. The reaction was quenched with water and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2S04, and concentrated. The crude product was purified by chromatography (hexanes to 10:90 EA/Hex) to afford the product in 17% yield (28 mg, 0.17 mmol).

The synthetic route of 53078-85-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE UNITED STATES OF AMERICA; UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL; BOXER, Matthew Brian; ROHDE, Jason Matthew; PRAGANI, Rajan; LIU, Li; DAVIS, Mindy Irene Emily; BRIMACOMBE, Kyle Ryan; SHEN, Min; SIMEONOV, Anton; KARAVADHI, Surendra; URBAN, Daniel Jason; JADHAV, Ajit; WANG, Xiaodong; MCIVER, Andrew Louis; (407 pag.)WO2016/106331; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 766-46-1, A common heterocyclic compound, 766-46-1, name is 2′-Bromophenylacetylene, molecular formula is C8H5Br, 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 solution of sulfonyl azides 1 (0.6 mmol), o-bromo-phenylacetylenes 2 (0.5 mmol), aromatic amines 3 (0.55 mmol), and CuI (0.05 mmol) in DMSO (2 mL) in Schlenk tube was added TEA (0.5 mmol) slowly via a syringe. The reaction solution was stirred at room temperature under N2 for 2 h. The solution was then added to CuI (0.05 mmol), K2CO3 (1 mmol), and l-proline (0.2 mmol), and the mixture was stirred at 60 C under N2 for 4 h. The reaction mixture was partitioned between ethyl acetate and saturated aq NH4Cl, the organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography on silica gel with petroleum ether and ethyl acetate (6:1 to 9:1).

The synthetic route of 766-46-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jin, Hongwei; Zhou, Bingwei; Wu, Zhi; Shen, Yang; Wang, Yanguang; Tetrahedron; vol. 67; 6; (2011); p. 1178 – 1182;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 418762-26-2, name is 4-Bromo-2-fluoro-5-methylaniline, belongs to bromides-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 418762-26-2, Quality Control of 4-Bromo-2-fluoro-5-methylaniline

Example 51A N,N-dibenzyl-4-bromo-2-fluoro-5-methylbenzenamine A suspension of 4-bromo-2-fluoro-5-methylbenzenamine (1 g, 4.9 mmol),(bromomethyl)benzene (2.5 g, 14.7 mmol) and potassium carbonate (2 g, 14.7 mmol) in acetonitrile (80 mL) was heated in a sealed tube at 100C for 16 hours. After concentration, the residue was diluted with ethyl acetate (80 mL), washed with water (20 mL), dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography on silica gel (200-300 mesh) eluting with 50/1 petroleum ether/ethyl acetate to give the title compound. MS : 384 (M+H+).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; ABBOTT LABORATORIES; ABBOTT LABORATORIES TRADING (SHANGHAI) COMPANY, LTD.; VASUDEVAN, Anil; PENNING, Thomas Dale; CHEN, Huanming; LIANG, Bo; WANG, Shaohui; WU, Fengchun; SHEN, Yan; LIU, Cuihua; ZOU, Zhenguang; WO2012/97684; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 22385-77-9, name is 1-Bromo-3,5-di-tert-butylbenzene, belongs to bromides-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 22385-77-9, Application In Synthesis of 1-Bromo-3,5-di-tert-butylbenzene

An oven-dried 500 mt_ round bottom flask equipped with a magnetic stir bar and rubber septum was attached to a double manifold and cooled under vacuum. The flask was backfilled with N2, the rubber septum was removed, l-bromo-3,5-di-te/t- butylbenzene (32.4 g, 120 mmol, 3.01 equiv.) was added, and the septum replaced. The flask was then purged with N2 for 15 minutes. THF (240 ml_, [0.5 M]) was added and the flask was cool to -78 C in a dry ice/acetone bath. While stirring, nBuLi (48.2 mL, 120 mmol, 3 equiv., [2.49 M] in hexanes) was added dropwise via syringe pump over 30 minutes. PCI3 (3.5 mL, 40 mmol, 1 equiv.) was added dropwise via syringe pump over 15 minutes. After the addition was complete, the flask was warmed to 0 C in an ice/water bath and stirred for 4 hours. The flask was allowed to warm to RT, the septum was removed and the reaction was quenched by adding brine (100 mL). The reaction was poured into a separatory funnel and the product was extracted 2X with Et20 (100 mL) . The organic layer was dried over MgS04, filtered through a glass frit, and the solvent removed in vacuo. The product was purified by recrystallization from hot EtOH (200 mL), cooled under ambient conditions, then placed in a -20 C freezer overnight. Collection of the solid via filtration and washing with EtOH resulted in white crystals ( 10.6 g, 44% yield) : 1H NMR (600 MHz, CDCl3) delta 7.38 (t, J = 1.8 Hz, 3H), 7.12 (dd, J = 8.5, 1.8 Hz, 6H), 1.22 (s, 54H) ; 13C NMR ( 151 MHz, CDCl3) delta 150.6 (d, J = 6.7 Hz), 137.3 (d, J = 9.4 Hz), 128.1 (d, J = 19.3 Hz), 122.4 , 35.0 , 31.5; 31P NMR (243 MHz, CDCl3) delta -3.59; FTIR (cm 1) : 2963, 1589, 1577, 1362, 1249, 1130, 875, 710; mp = 145-147 C; HRMS (LIFDI) m/z, calculated for [C42H63P] + : 598.4667; found : 598.4688.

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-3,5-di-tert-butylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UNIVERSITY OF DELAWARE; WATSON, Donald; CINDERELLA, Andrew; VULOVIC, Bojan; (76 pag.)WO2018/64163; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 615-59-8,Some common heterocyclic compound, 615-59-8, name is 1,4-Dibromo-2-methylbenzene, molecular formula is C7H6Br2, 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.

Under argon atmosphere, 0.65 g (0.80 mmol) of PdCl2(dppf),5.9 g (60.0 mmol) of potassium acetate, and 15.2 g (60.0 mmol)bis(pinacolato)diboron were weighed into a 100 mL two-neck flask. 5.0 g (20.0 mmol) of 1,4-dibromo-2-methylbenzene and 100mL dry1,4-dioxane were added to the solution. After stirring at 100 C for24 h, the solution was stirred further night at room temperature, and the solvent was removed in vacuum. The residue was purified by column chromatography using silica gel (n-hexane/ethyl acetate 50:1). The product was recrystallized with dichloromethane andethanol. The product was a white solid. Yield: 5.1 g (74%). 1H NMR d:7.76 (s, 1H), 7.61 (s, 2H), 2.55 (s, 3H), 1.36 (s, 24H). 13C NMR d:143.83, 135.87, 135.03, 130.84, 83.78, 83.50, 77.46, 77.04, 76.61,24.90, 24.87, 22.03. MS (EI) m/z: 344.3(M).

The synthetic route of 615-59-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Park, Soyun; Tan, Xiaofeng; Jang, Woongsik; Cho, Jae Sang; Kim, Yun-Hi; Kwon, Soon-Ki; Wang, Dong Hwan; Organic electronics; vol. 46; (2017); p. 183 – 191;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 54962-75-3, 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. 54962-75-3 name is 3-Bromo-5-(trifluoromethyl)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.

Reference Example 68 1-[3-bromo-5-(trifluoromethyl)phenyl]pyrrolidin-3-ol; 3-Bromo-5-(trifluoromethyl)aniline (5.0 g) and 1,4-dibromobutan-2-ol (4.83 g) were stirred at 100C for 3 hr. After cooling to room temperature, to the reaction mixture was added saturated aqueous sodium carbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate 90:10 – 50:50) to give the title compound (5.6 g, yield 22%) as a brown oil. 1H-NMR (300 MHz, CDCl3)delta:1.66 (br. s, 1 H), 2.08 – 2.27 (m, 2 H), 3.23 – 3.32 (m, 1 H), 3.38 (td, J = 8.8, 3.4 Hz, 1 H), 3.44 – 3.59 (m, 2 H), 4.65 (br. s, 1 H), 6.65 (s, 1 H), 6.80 (t, J = 1.9 Hz, 1 H), 7.02 (s, 1 H).

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

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2295406; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 944718-31-4, These common heterocyclic compound, 944718-31-4, name is 5-Bromo-1-methyl-1H-benzo[d][1,2,3]triazole, 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.

5-Bromo-1-methyl-benzotriazole (500.00 mg, 2.36 mmol), Pd(OAc)2 (52.98 mg,236.00 umol), tris-o-tolylphosphane (143.66 mg, 472.00 umol), DIPEA (915.02 mg,) in DMF (8.00 mL) was added methyl prop-2-enoate (2.03 g, 23.60 mmol, 2.12 mL), DIPEA (915.02 mg, 7.08 mmol, 1.24 mL) and degassed and microwaved at 130 C for 2h. After filtration through celite and diluted with EtOAc, the solution was washed with water and brine and dried over Na2SO4. Si gel chromatography gave methyl (E)-3-(1- methylbenzotriazol-5-yl)prop-2-enoate (240 mg, 47% yield). LCMS: Rt = 1.04 mm, mlz =218.

Statistics shows that 5-Bromo-1-methyl-1H-benzo[d][1,2,3]triazole is playing an increasingly important role. we look forward to future research findings about 944718-31-4.

Reference:
Patent; BIOGEN MA INC.; CAPACCI, Andrew, George; DECHANTSREITER, Michael; ENYEDY, Istvan; JONES, John, H.; LIN, Edward, Yin-Shiang; LUCAS, Brian, Stuart; MA, Bin; (273 pag.)WO2018/140876; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 698-00-0, 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. 698-00-0, name is 2-Bromo-N,N-dimethylaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a stirred solution of N,N-dimethylanilines (1, 1.0 mmol) and 2,3-dihydrofuran (2, 10 mmol) in MeCN(20 ml), Co(ClO4)2 (10 mol%) was added. The reactions were performed at 50 C under oxygen atmosphere(O2 balloon) and completed in 48 hours. The products 3 were isolated by flash column chromatographic separation (acetone/petroleum ether = 1:40 to 1:30).

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-Bromo-N,N-dimethylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Huo, Congde; Chen, Fengjuan; Quan, Zhengjun; Dong, Jie; Wang, Yajun; Tetrahedron Letters; vol. 57; 46; (2016); p. 5127 – 5131;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 74586-53-1, name is 3-Bromo-5-methylaniline, belongs to bromides-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 74586-53-1, Quality Control of 3-Bromo-5-methylaniline

[0251] 3-Bromo-5-methylaniline (372.2 mg, 2.0 mmol) was dissolved in aqueous 1 N hydrochloric acid (160 mL), and acrolein diethylacetal (762 mu^, 5.0 mmol) was added. The reaction mixture was heated to reflux for 24 hours. After cooling to room temperature, the dark brown solution was neutralized with solid potassium carbonate and extracted with dichloromethane (3 x 150 mL). Combined organic layers were washed with brine (1 x 150 mL), dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified on silica gel using a mixture of dichloromethane and methanol (100:0 to 90: 10 gradient) as eluent. The product was obtained as brown oil as a mixture of isomers Int-2 and Int-2A (1.5: 1) in 35% yield. Major isomer: ‘H- MR (500 MHz, CDC13): delta 8.88 (dd, J = 4.2, 1.3 Hz, 1H), 8.46 (d, J = 8.5 Hz, 1H), 7.85 (s, 1H), 7.68 (s, 1H), 7.42 (dd, J= 8.5, 4.2 Hz, 1H), 2.65 (s, 3H); Minor isomer: 1H-NMR (500 MHz, CDC13): delta 8.90 (dd, J = 4.1, 1.4 Hz, 1H), 8.27 (d, J = 8.5 Hz, 1H), 8.14 (s, 1H), 7.48 (s, 1H), 7.42 (dd, J = 8.5, 4.2 Hz, 1H), 2.54 (s, 3H).

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

Reference:
Patent; ACTAVALON, INC.; DNEPROVSKAIA, Elena, V.; HOLZWARTH, Michael, S.; RYCHNOVSKY, Scott, D.; (184 pag.)WO2018/85348; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary