Month: May 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. 627526-90-3, name is 1-Bromo-3-(difluoromethyl)-5-fluorobenzene, A new synthetic method of this compound is introduced below., Computed Properties of C7H4BrF3

To a solution of magnesium (165 mg, 6.81 mmol) and lithium chloride (144 mg, 3.40 mmol) in THF (6.0 mL) was added DIBAL-H (27.2 muL, 0.027 mmol). After 5 minutes at room temperature, the reaction mixture was cooled to 0 C, and 1-bromo-3-(difluoromethyl)-5- fluorobenzene (612 mg, 2.72 mmol) was added at 0 C. The resulting mixture was stirred at 0 C for 1 hour, and then the mixture was added to a solution of (2S,3S,4R,5R)-5-(4-chloro-7H- pyrrolo[2,3-d]pyrimidin-7-yl)-2-(methoxy(methyl)carbamoyl)-3-methyltetrahydrofuran-3,4-diyl diacetate (200 mg, 0.454 mmol) in THF (3.0 mL) at 0 C. The resulting mixture was stirred for 10 minutes at 0 C. The reaction was quenched with acetic acid (390 muL, 6.81 mmol), and the resulting mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and then washed with 1 N citric acid. The organic layer was dried over Na2SO4, and the organic solvent was removed under reduced pressure. The crude material was then purified by flash column chromatography (EtOAc/EtOH (3:1) in hexanes, 5 to 100%) to yield (2S,3S,4R,5R)-5-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-(3-(difluoromethyl)-5- fluorobenzoyl)-3-methyltetrahydrofuran-3,4-diyl diacetate as a solid. MS: 526 [M+H]+.

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; MERCK SHARP & DOHME CORP.; MACHACEK, Michelle; WITTER, David; HUANG, Chunhui; KAWAMURA, Shuhei; SCHNEIDER, Sebastian; WAN, Murray; (117 pag.)WO2020/33285; (2020); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 6698-13-1, name is 4-Bromo-1,3-benzodioxole, molecular formula is C7H5BrO2, 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: C7H5BrO2

General procedure: An oven dried pressure tube was charged with aryl halide (0.5mmol), CuI (10-25mol%), anhydrous Zn(OAc)2 (1.5-2equiv) and anhydrous DMSO (1.6mL). The tube was sealed with a Teflon screw cap and stirred at 135C for 24-36h. The reaction mixture was then cooled to room temperature and stirred in 10mL of diethyl ether for 5min. It is filtered through a sintered funnel and the filtrate is washed with excess ice cold water and further extracted with diethyl ether (3¡Á10mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to give the crude product, which was purified by column chromatography using 200-400 mesh silica gel and a mixture of diethyl ether and hexane (or pentane, for Table 2, entries 2, 8, 10, 14, 16 and 24) as eluents to afford the desired products in good yields.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6698-13-1, its application will become more common.

Reference:
Article; Joseph, P.J. Amal; Priyadarshini; Kantam, M. Lakshmi; Sreedhar; Tetrahedron; vol. 69; 38; (2013); p. 8276 – 8283;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 627463-18-7, name is 4-Bromo-1-ethyl-2-fluorobenzene, A new synthetic method of this compound is introduced below., COA of Formula: C8H8BrF

To a stirred solution of 4-bromo-1-ethyl-2-fluoro-benzene (1.80 g, 8.86 mmol) in N,N-dimethylformamide (20 mL), under a nitrogen atmosphere was added PdCl2(PPh3)2, CuI, and LiCl. The mixture was stirred at 60 C. for 3 hours, then poured into water and extracted with ether (3*20 mL). The extract was dried (Na2SO4) and concentrated. The residue was filtered through a pad of silica gel eluding with hexanes. Removal of solvent gave the crude, 1.67 g, which was used for the next step.

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; Chu, Xin-Jie; Ding, Qingjie; Jiang, Nan; Kim, Kyungjin; Lovey, Allen John; McComas, Warren William; Mullin JR., John Guilfoyle; Tilley, Jefferson Wright; US2004/6058; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 1083181-43-4, name is 6-Bromo-1-methyl-1H-benzo[d][1,2,3]triazole, This compound has unique chemical properties. The synthetic route is as follows., Formula: C7H6BrN3

The title compound is prepared according to General Procedure 8 described for Intermediate 14, using 6-bromo-1-methyl-1 H-1 ,2,3-benzotriazole (Intermediate 80, 45 mg; 0.21 mmol; 1 eq.), bis(pinacolato)diboron (108 mg; 0.42 mmol; 2 eq.), potassium acetate (125 mg; 1.27 mmol; 6 eq.), Pd(dppf)CI2 (27 mg; 0.03 mmol; 0.15 eq.) in DMSO (2 mL). Conditions: 90 C overnight. The crude 1-methyl-6-(tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 – – 1 ,2,3-benzotriazole (80 mg; 0.10 mmol; 45%; brown solid; UPLC purity: 85%) is used in the next step without further purification.

According to the analysis of related databases, 1083181-43-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SELVITA S.A.; FABRITIUS, Charles-Henry Robert Yves; NOWAK, Mateusz Oktawian; WIKLIK, Katarzyna Anna; SABINIARZ, Aleksandra Barbara; BIE?, Marcin Dominik; BUDA, Anna Malgorzata; GUZIK, Pawel Szczepan; BIA?AS, Arkadiusz Kacper; PAWLIK, Henryk Edward; BOUTARD, Nicolas Felix Pierre; (439 pag.)WO2016/180537; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 945244-29-1, A common heterocyclic compound, 945244-29-1, name is 5-Bromo-2-fluoro-4-methylaniline, molecular formula is C7H7BrFN, 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.

Combine 5-bromo-2-fluoro-4-methylaniline (3.1 g, 15.2 mmol), bis(pinacolato)diboron (4.24 g, 16.7 mmol), and potassium acetate (4.47 g, 45.6 mmol) in dioxane (40 mL) and sparge with argon. Add [l,l’-bis(diphenylphosphino)ferrocene]- dichloropalladium(II)-dichloromethane complex (0.620 g, 0.760 mmol), sparge again with argon and heat at 100C overnight. Filter the reaction mixture and concentrate in vacuo. Purify by silica gel chromatography (EtOAc/hexanes) to give the title compound (3.24 g, 85%). MS (m/z): 252.1 (M+ H+).

The synthetic route of 945244-29-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DECIPHERA PHARMACEUTICALS, LLC; ELI LILLY AND COMPANY; FLYNN, Daniel L.; KAUFMAN, Michael D.; VOGETI, Lakshminarayana; WISE, Scott C.; LU, Wei-Ping; SMITH, Bryan D.; CALDWELL, Timothy M.; PATT, William C.; HENRY, James Robert; HIPSKIND, Philip Arthur; PENG, Sheng-Bin; WO2013/134298; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 21865-50-9, name is 6-Bromo-2,3,4,9-tetrahydro-1H-carbazole, A new synthetic method of this compound is introduced below., HPLC of Formula: C12H12BrN

To a solution of 6-bromo-2,3,4,9-tetrahydro-lH-carbazole (150 mg, 0.61 mmol) inDMF (5 ml) was added NaH (60% in mineral oil, 37 mg, 0.92 mmol) and tetrabutylammonium iodide (340 mg, 0.92 mmol). The resulting mixture was stirred at room temperature for 10 min and followed by addition of l-(3-chloropropoxy)-3,5- dimethylbenzene (121 mg, 0.61 mmol). The reaction mixture was stirred at room temperature overnight, poured into H2O (30 ml), and extracted with EtOAc (3 x 30 ml). The organic layers were combined, dried over MgSO4, filtered and cone, in vacuo. The crude product was purified by silica gel flash chromatography (EtOAc/hexane, 0-20%) to give the title compound (colorless oil, 182 mg). The yield: 72.4%.

The synthetic route of 21865-50-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ITHERX PHARMACEUTICALS, INC.; WO2009/103022; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 51776-71-7, name is 1-Bromo-4-(difluoromethyl)benzene, 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 51776-71-7, Quality Control of 1-Bromo-4-(difluoromethyl)benzene

(1) A solution of 1-bromo-4-(difluoromethyl)benzene (5.00 g, 24.1 mmol) in THF (75 mL) was cooled to -78 C. while stirring, and a solution of n-butylithium in n-hexane (1.57 M, 16.9 mL, 26.6 mmol) was added dropwise and the resultant mixture was stirred for 30 minutes. After adding DMF (4.09 mL, 53.1 mmol) and elevating the temperature to 0 C. over 1 hour, the resultant solution was stirred for 14 hours while gradually returning the temperature to room temperature. The reaction solution was neutralized by adding an ammonium chloride aqueous solution and extraction was performed with diethyl ether twice. Organic fractions were combined and washed with a saturated salt solution and dried over magnesium sulfate. The solvent was removed by distillation under reduced pressure and the resultant residue was purified by column chromatography to obtain 4-(difluoromethyl)benzaldehyde (2.49 g, 66%). 1H-NMR (CDCl3) delta: 10.08 (1H, s), 7.99 (2H, d, J=8.3 Hz), 7.70 (2H, d, J=8.3 Hz), 6.72 (1H, t, J=55.9 Hz).

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; Teijin Pharma Limited; HOSODA, Shinnosuke; UNOKI, Gen; WATANABE, Hidekazu; SASAKI, Kosuke; SHIBATA, Jun; YOKOYAMA, Emi; HORIE, Kyohei; TAKAGI, Kenichiro; (202 pag.)US2019/31628; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 51776-71-7, name is 1-Bromo-4-(difluoromethyl)benzene, A new synthetic method of this compound is introduced below., Product Details of 51776-71-7

Step 2: To a 250mL round-bottom flask was added 150mL toluene, compound 12b (19g, 0.09mol, l .Oq), Benzyl mercaptan (12.5g, O. lmol, l . leq), DIPEA (23.7g, 0.18mol, 2.0eq), [l, -bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (3.7g, 0.005mol, 0.05eq) and 4,5- bis(diphenylphosphino)-9,9-dimethylxanthene (5.3g, 0.009mol, O. leq). The reaction was heated to reflux for 15h. The reaction mixture was concentrated in vacuum and purified by column chromatography on silica gel eluted to afford the title compound 12c (15g). Yield: 65%.

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; LIANG, Congxin; (62 pag.)WO2018/5713; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 1435-54-7, These common heterocyclic compound, 1435-54-7, name is 1,3-Dibromo-2-fluorobenzene, 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.

2-isopropylphenol 0.1 mol,Dissolved in 100 mL of anhydrous tetrahydrofuran,Stirring, accurately weighing 0.4 moles of sodium hydride in batches added to the reaction flask,Do not be too fast to prevent too much bubble generated, plus the solution after the yellow,Then add 1,3-dibromo-2-fluorobenzene 0.11mol, also added in batches, room temperature reaction overnight. The resulting reaction product was filtered,Remove the solid material, the filtrate spin dry, add methylene chloride dissolved,Column column with petroleum ether: ethyl acetate = 1: 5 (volume ratio)To give 1,3-dibromo-2- (2-isopropylphenoxy) benzene (Intermediate A-1) (0.05 mol, y = 50%).

The synthetic route of 1435-54-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jilin Optical and Electronic Materials Co., Ltd.; Cui, Dunzhu; Gao, Chunji; Wang, Hui; Ma, Xiaoyu; Li, Ming; Li, Wenju; (54 pag.)CN106187963; (2016); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 952511-74-9,Some common heterocyclic compound, 952511-74-9, name is 4-Bromo-3-methylbenzene-1,2-diamine, molecular formula is C7H9BrN2, 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.

4-Bromo-3-methyl-1,2-benzenediamine (6.89 g, 34.3 mmol), formic acid (60 ml) and 37percent concentrated HCl (150 ml) were heated at 60¡ã C. for 12 h, cooled in an ice-water bath, and slowly adjusted with 28percent concentrated ammonium solution (280 ml) to pH8-9. The solid was collected by filtration, washed with water and dried in air to afford the title compound as a pinkish white solid.1H NMR (400 MHz, DMSO-d6) delta ppm 2.58 (s, 3H) 7.32 (s, 2H) 8.20 (s, 1H) 12.62 (br., 1H); (M+1) 212.94, 1.11 min (LC/MS method A)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-3-methylbenzene-1,2-diamine, its application will become more common.

Reference:
Patent; Diaz, Caroline Jean; Haffner, Curt Dale; Speake, Jason Daniel; Zhang, Cunyu; Mills, Wendy Yoon; Spearing, Paul Kenneth; Cowan, David John; Green, Gary Martin; US2010/222345; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary