Author: Jessica.F

Synthetic Route of 1435-54-7, A common heterocyclic compound, 1435-54-7, name is 1,3-Dibromo-2-fluorobenzene, molecular formula is C6H3Br2F, 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.

To a solution of 1,3-dibromo-2-methylbenzene (1 equiv) in DMF/EtsN (1 : 1) is added Pd(PPh3)4 (3 mol %) and 4-ethynylbenzonitrile (2 equiv), and the mixture is stirred for 5 minutes. Sodium ascorbate (6 mol % in DMF) and CuS04 (1 mol % in DMF) are then added, and the reaction is stirred at 80 C for 4 hours. The reaction is diluted with EtOAc and washed with saturated NTfiCl solution and brine. The organic layer is dried over anhydrous Na2S04, filtered, and concentrated under reduced pressure. The crude residue is purified by column chromatography on silica gel to provide 4,4′-((2-fluoro-1,3-phenylene)bis(ethyne-2,1- diyl))dibenzonitrile.

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

Reference:
Patent; GEORGIA STATE UNIVERSITY RESEARCH FOUNDATION, INC.; WANG, Binghe; BOYKIN, David, W.; CHOUDHARY, Manjusha, Roy; KUMAR, Arvind; YU, Bingchen; ZHU, Mengyuan; (498 pag.)WO2019/241566; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

1435-54-7, name is 1,3-Dibromo-2-fluorobenzene, belongs to bromides-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. name: 1,3-Dibromo-2-fluorobenzene

General procedure: Scheme 4-1: In Step 1 the appropriately substituted dibromo species is coupled with an appropriate boronic acid as known in the art to form a mixture of biaryl and triaryl products from which the desired biaryl compound is isolated. In Step 2 the appropriately substituted biaryl species is converted to the Grignard reagent with activated magnesium. In Step 3 the appropriately substituted aldehyde is treated with the previously prepared Grignard reagent to form an alcohol. In Step 4 the appropriately substituted alcohol is converted to a bromide as known in the art with carbon tetrabromide and triphenyl phosphine. In Step 5 the appropriately substituted bromide is converted to the Grignard reagent with activated magnesium.

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

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAL, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; GREENLEE, William; (340 pag.)WO2017/35415; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 1379295-90-5, name is 2-Bromo-4,5,6,7-tetrahydrobenzo[d]thiazol-6-amine, 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 1379295-90-5, HPLC of Formula: C7H9BrN2S

Step (ii): Preparation of N-(2-Bromo-4^,6,7-tetrahydro-benzothiazol-6-yl)-propionamide A solution of 2-Bromo-4,5,6,7-tetrahydro-benzothiazol-6-ylamine (0.36 grams, 1.5 mmol, obtained in above step) and triethylamine (0.43 mL, mmol) in dichloromethane (15 mL) was cooled to 0 C. Propionylchloride (0.17 mL, 1.8 mmol) in dichloromethane (2 mL) were added and stirred the reaction mass for 30 minutes. After completion of reaction, the mass was poured onto ice cold water and the product was extracted with ethyl acetate (3 x 15 mL). Thecombined organics were washed with water followed by brine, dried over anhydrous sodium sulphate and the organic volatiles were evaporated under vacuum. The residue was purified by flash chromatography (methanol / chloroform, 2 / 98) to obtain the title compound (0.4 grams). – NMR (delta ppm): 0.81 – 0.85 (1H, m), 1.14 – 1.18 (3H, m), 1.20 – 1.28 (2H, m), 1.90 – 1.96 (1H, m), 2.02 – 2.05 (1H, m), 2.18 – 2.23 (2H, m), 2.57 – 2.63 (1H, m), 2.86 – 2.91 (1 H, m), 3.10 – 3.15 (lH, m);Mass (m/z): 289.2 (M+H)+, 291.2 (M+3H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-4,5,6,7-tetrahydrobenzo[d]thiazol-6-amine, and friends who are interested can also refer to it.

Reference:
Patent; SUVEN LIFE SCIENCES LIMITED; NIROGI, Ramakrishna; SHINDE, Anil, Karbhari; KAMBHAMPATI, Ramasastri; NAMALA, Rambabu; DWARAMPUDI, Adi, Reddy; KOTA, Laxman; GAMPA, Murlimohan; KODRU, Padmavathi; TIRIVEEDHI, Taraka, Naga, Vinaykumar; KANDIKERE, Vishwottam, Nagaraj; MUDDANA, Nageshwara, Rao; SARALAYA, Ramanatha, Shrikantha; JAYARAJAN, Pradeep; SHANMUGANATHAN, Dhanalakshmi; AHMAD, Ishtiyaque; JASTI, Venkateswarlu; WO2012/29070; (2012); 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. 179737-33-8, name is 2,3-Dibromo-1,4-difluorobenzene, A new synthetic method of this compound is introduced below., Recommanded Product: 179737-33-8

1,2-dibromo-3,6-difluorobenzene (50.0 g, 183.9 mmol), 2-methoxyphenylboronic acid (67.1 g, 441.4 mmol), a 2 M aqueous solution of Na2CO3 (368 mL, 736 mmol), DME (370 mL), toluene (370 mL), and Pd [PPh3]4 (21.3 g, 18. 4 mmol) were loaded into a three-necked flask, and the mixture was refluxed under an Ar atmosphere for 8 hours. After the completion of the reaction, the resultant was cooled to room temperature. The resultant sample was transferred to a separating funnel, and water (500 mL) was charged into the funnel. Then, the mixture was extracted with CH2Cl2. The extract was dried with MgSO4, and was then filtrated and concentrated. The resultant sample was purified by silica gel column chromatography, whereby a white solid was obtained in an amount of 30.6 g in 51% yield. FD-MS C20H16F2O2: theoretical value 326, observed value 326

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; Idemitsu Kosan Co., Ltd.; EP2301921; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 202865-77-8, 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. 202865-77-8, name is 2-Bromo-4-fluoro-6-methylaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a suspension of 2-bromo-4-fluoro-6-methylaniline (5 g, 24.51 mmol) in hydrochloric acid (8 M, 22 mL, 176 mmol) at 0 C. was added a solution of sodium nitrite (1.78 g, 25.7 mmol) in water (ca. 5.5 mL) dropwise. After 10 min, the resulting solution was neutralized (pH 4-5) by addition of solid sodium acetate. The resulting solution was added to a solution of 2-methyl-2-propanethiol (2.76 mL, 24.5 mmol) in ethanol (57 mL) at 0 C. The resulting mixture was stirred at 0 C. for 30 min. The resulting mixture was poured onto ice and the resulting mixture was extracted into diethyl ether (2×). The ethereal was washed with water, then brine, dried over magnesium sulfate, and concentrated. The resulting residue was dissolved in dimethylsulfoxide (14 mL) and transferred to a solution of potassium tert-butoxide (22 g, 196 mmol) in dimethylsulfoxide (140 mL) in a cool water bath (ca. 10 C.) via canula. The bath was removed and stirring continued for 30 min. The reaction mixture was poured onto ice/concentrated hydrochloric acid. The resulting mixture was extracted with dichloromethane (2×), washed with water (3×), then brine, dried over magnesium sulfate and concentrated. Prep HPLC gave 1.66 g (31.5%) as a pale solid. LC/MS (HPLC method 3): tR=2.337 min, 215.01(MH)-.

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-4-fluoro-6-methylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bristol-Myers Squibb Company; US2009/18132; (2009); 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. 128259-68-7, name is 1,3-Dibromo-2,5-difluorobenzene, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1,3-Dibromo-2,5-difluorobenzene

A mixture of 1,3-dibromo-2,5-difluorobenzene (4 g, 14.7 mmol), benzophenone imine (2.6 mL, 15.5 mmol), sodium tert-butoxide (2.1 g, 22.1 mmol), (S)-BINAP (1.4 g, 2.2 mmol), in toluene (15 mL) was sparged with Argon and charged with Pd2(dba)3 (0.67 g, 0.74 mmol). The reaction was then sealed and irradiated at 100° C. for 30 minutes in a microwave reactor. The reaction mixture was diluted with Et2O and stirred for 2 hours with a palladium scavenger (Siliabond DMT). The mixture was filtered through a plug of Celite and the collected filtrate was partitioned between diethyl ether and water, and the resulting layers separated. The organic portion was washed with water, brine, dried (MgSO4), and concentrated to afford a brown red solid. The solid was dissolved in THF (40 mL) and treated with aqueous 6.0 N HCl solution (25 ml, 150 mmol). The reaction was stirred for 1.5 hours at room temperature was partitioned between water and Et2O. The layers were separated and the aqueous portion was brought to a pH of 9 with aqueous 1.0 M NaOH solution. The basic aqueous layer was extracted diethyl ether (3*30 mL) the combined diethyl ether layers were washed with aqueous 1.0 M NaOH solution, water, brine, dried (MgSO4), concentrated. Purification by flash chromatography (SiO2, 0-10percent EtOAc in heptane) afforded 3-bromo-2,5-difluoroaniline (1.7 g, 8.2 mmol, 56percent, trace benzophenone) as an orange solid: 1H NMR (400 MHz, CDCl3) delta 3.93 (br s, 2H) 6.43 (m, 1H) 6.62 (m, 1 H).

According to the analysis of related databases, 128259-68-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Costales, Abran Q.; Huang, Shenlin; Jin, Jeff (Xianming); Liu, Zuosheng; Pecchi, Sabina; Poon, Daniel; Tellew, John; US2011/52578; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 268733-18-2, These common heterocyclic compound, 268733-18-2, name is 4-Bromo-3,5-bis(trifluoromethyl)aniline, 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) 300 mg of 4-bromo-3,5-bis(trifluoromethyl)aniline was dissolved in 2 mL of toluene, and 130 mg of 3-thiophene carboxyaldehyde and then a catalytic amount of pyridinium p-toluene sulfonate were added and reacted at about 100C overnight, and then the reaction solution was left to cool. To the reaction solution, 50 mg of sodium borohydride and 2 mL of ethanol were added and reacted at room temperature for about two hours. Then, water and ammonium chloride were added in proper amounts, followed by stirring. A crude solution obtained by extraction with ethyl acetate was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=2/1) to obtain 340 mg of N-(4-bromo-3,5-bis(trifluoromethyl)phenyl)-3-thiophene methanamine (melting point: 78-79C).

The synthetic route of 268733-18-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ISHIHARA SANGYO KAISHA, LTD.; EP2172456; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 5279-32-3, These common heterocyclic compound, 5279-32-3, name is 5,6-Dibromobenzo[d][1,3]dioxole, 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.

Example 29: Preparation of N-(4-(6-bromobenzo[d] [l,3]dioxol-5-yl)phenyl)-2,6- difluorobenzamide (81):; Preparation of 4-(6-bromobenzo[d] [l,3]dioxol-5-yl)aniline (80):; Palladium tetrakis-triphenylphosphine (67 mg, 58 muiotaetaomicron) was added to a degassed solution of bromide 78 (323 mg, 1.15 mmol) and boronic acid 79 (200 mg, 1.15 mmol) in dioxane : acetonitrile : water (9:9:2, 7.6 mL) and potassium carbonate (679 mg, 3.2 mmol). The resulting mixture was heated under argon at 90 C with stirring for 1 h. The mixture was then cooled, diluted with dichloromethane (9 mL), dried with sodium sulfate and concentrated under reduced pressure. Flash chromatography (ISCO system, silica, 0-2.5% methanol in dichloromethane) provided 80 (150 mg, 45%) as a solid: LRESIMS m/z 292.1 [M+H]+, calcd. for Ci3H11Br1N102 292.0.

Statistics shows that 5,6-Dibromobenzo[d][1,3]dioxole is playing an increasingly important role. we look forward to future research findings about 5279-32-3.

Reference:
Patent; CALCIMEDICA, INC.; WHITTEN, Jeffrey P.; PEI, Yazhong; CAO, Jianguo; WANG, Zhijun; ROGERS, Evan; DYCK, Brian; GREY, Jonathan; WO2011/139765; (2011); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 6683-75-6, name is 1,2-Dibromo-4-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 6683-75-6, name: 1,2-Dibromo-4-tert-butylbenzene

In a three-necked flask equipped with a reflux tube, 292 g (1.0 mol) of p-tert-butyl o-dibromobenzene, 90 g (1.0 mol) of cuprous cyanide, 16.8 g (0.1 mol) of silver carbonate, and 52.4 g of copper acetylacetonate (0.2%) were added. 1460 mL of mol) and DBU were heated to 100 C. After the reaction, the insoluble material was filtered off and the DBU was recovered under reduced pressure. The residue was poured into water and filtered to give 95 g of p-tert-butylphthalonitrile. The yield was 51.6%.

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; Zhengzhou Gaike Technology Co., Ltd.; Guo Libing; (5 pag.)CN107903190; (2018); A;,
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. 5910-12-3, name is 3-Bromopyrazolo[1,5-a]pyridine, This compound has unique chemical properties. The synthetic route is as follows., Safety of 3-Bromopyrazolo[1,5-a]pyridine

4i4)4′)4’i5i5,5,,5′-Octamethyl-2,2′-bi(1 ,3,2-dioxaborolane) (1.27 g, 5.0 mmol), palladium (II) acetate (0.050 g, 0.228 mmol), tricyclohexylphosphine (0.127 g, 0.46 mmol), potassium carbonate (0.945 g, 6.84 mmol) and water (0.05 mL) were added to a solution of 3-bromopyrazolo[1 ,5-a]pyridine (Preparation 22c, 0.90 g, 4.56 mmol)) in diglyme (10 mL) and the resulting mixture was heated at 100 C for 2h. After cooling, the reaction mixture was filtered through Celite, eluting with methanol. The filtrate was evaporated and the crude product was used with no further purification in the next synthetic step.LRMS (m/z): 245 (M+1)+.

According to the analysis of related databases, 5910-12-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ALMIRALL, S.A.; BACH TA?A, Jordi; PAGES SANTACANA, Lluis, Miquel; TALTAVULL MOLL, Joan; EASTWOOD, Paul, Robert; GONZALEZ RODRIGUES, Jacob; GIULIO MATASSA, Victor; WO2011/101161; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary