Author: Jessica.F

Application of 73908-04-0, 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 73908-04-0 as follows.

General procedure: An oven-dried Schlenk tube containing a stirring bar was charged with NiI2 (2.5-10.0 mol%), L1 (4.4-17.6 mol%) and Mn powder (3 equiv.). The Schlenk tube was then evacuated and back-filled under a CO2 flow (this sequence was repeated three times) and finally an atmospheric pressure of CO2 was established. The corresponding alkyl bromide (0.5 mmol) and DMF (1 M) were added under a CO2 flow. Once added, the Schlenk tube was closed at atmospheric pressure of CO2 (1 atm) and stirred at the desired temperature for 20-48 h. The mixture was then carefully quenched with 2 M HCl to hydrolyse the resulting carboxylate and extracted with EtOAc (three times). The combined organic layer was washed with brine (three times), dried over anhydrous MgSO4, filtrated and evaporated. The resulting crude carboxylic acid was purified by conventional flash chromatography in silica gel using hexanes/EtOAc 3:1 with 1% formic acid.

According to the analysis of related databases, 73908-04-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Julia-Hernandez, Francisco; Moragas, Toni; Cornella, Josep; Martin, Ruben; Nature; vol. 545; 7652; (2017); p. 84 – 88;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 268733-18-2, A common heterocyclic compound, 268733-18-2, name is 4-Bromo-3,5-bis(trifluoromethyl)aniline, molecular formula is C8H4BrF6N, 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)1.0 g of 3,5-bis(trifluoromethyl)-4-bromoaniline was dissolved in 3 mL of hexamethylphosphoric acid triamide, and 730 mg of copper cyanide was added and reacted at 140C for 8 hours under irradiation with microwaves. The reaction solution was left to cool, and then, to the reaction solution, water and ethyl acetate were added, whereupon an insoluble solid content was removed by filtration through cerite. The organic layer was separated, and the aqueous layer was extracted twice with ethyl acetate. The organic layers were put together and washed with a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=5/2) to obtain 550 mg of 3,5-bis(trifluoromethyl)-4-cyanoaniline as white solid.

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

Electric Literature of 41825-73-4, 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. 41825-73-4 name is 2-Bromo-4,6-dimethylaniline, 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.

Production Example 1-40 Production of Compound Represented by Formula (1-41) Production of Compound Represented by Formula 3-1 2.04 g of 1,1?-bis(diphenylphosphino) ferrocene-palladium(II) dichloride-dichloromethane complex, 48.8 g of cesium carbonate, and 10 g of the compound represented by Formula (5-1) were dissolved in 125 ml of N,N-dimethylformamide at room temperature in a nitrogen atmosphere. 32.5 ml (1.0 M hexane solution) of triethylborane was added dropwise to the obtained solution, followed by stirring at room temperature for 16 hours in a nitrogen atmosphere. After the reaction liquid was filtered using Celite (registered trademark), water was added to the filtrate, the resultant product was extracted with tert-butyl methyl ether, and the organic layer was washed with a saturated saline solution, and dried over anhydrous magnesium sulfate. The obtained organic layer was concentrated under reduced pressure, and the resultant product was subjected to silica gel column chromatography (eluent, ethyl acetate_hexane=1:19?1:9), whereby 3.18 g of the compound represented by Formula (3-1) was obtained. 1H NMR (CDCl3) delta ppm: 6.78 (2H, s), 3.49 (2H, s), 2.51 (2H, q), 2.23 (3H, s), 2.16 (3H, s), 1.24 (3H, t)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-4,6-dimethylaniline, and friends who are interested can also refer to it.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; Jin, Yoshinobu; Fujino, Yoshimi; US2015/289505; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 376646-62-7, 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. 376646-62-7, name is (4-Bromo-2-methylphenyl)methanamine, This compound has unique chemical properties. The synthetic route is as follows.

[0196j A mixture of 2-(tert-butyl)thiazole-5-carboxylic acid (185 mg, 1.0 mmol), HBTU (455 mg, 1.2 mmol) and DIPEA (387 mg, 3.0 mmol) in DMF (5 mL) was stirred at rt for 15 mill. Then (4-bromo-2-methylphenyl)methanamine (300 mg, 1.5 mmol) was added. The resulting mixture was stirred at rt for 16 h. After diluted with water (40 mL), the mixture was extracted with EtOAc (80 mL x 2). The organic phase was concentrated and the residue was purified by silica gel column chromatography (petroleum ether/EtOAc = 10:1 4: 1) to give N-(4-bromo-2- methylbenzyl)-2-(tert-butyl)thiazole-5-carboxamide (220 mg, yield: 60percent) as a yellow solid. ESIMS (M+H) : 367.1. ?H NMR (400 MHz, CDC13) 5: 8.20 (s, 1H), 7.35 (d, J = 1.6 Hz, 1H), 7.32 (dd,J= 8.0, 1.6 Hz, 1H), 7.17 (d,J= 8.4 Hz, 1H), 4.55 (d,J= 5.6 Hz, 2H), 2.34 (s, 3H), 1.47 (s, 9H).

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

Reference:
Patent; BIOGEN IDEC MA INC.; SUNESIS PHARMACEUTICALS, INC.; HOPKINS, Brian, T.; MA, Bin; CHAN, Timothy, Raymond; SUN, Lihong; ZHANG, Lei; KUMARAVEL, Gnanasambandam; LYSSIKATOS, Joseph, P.; KOCH, Kevin; MIAO, Hua; WO2015/89337; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 6134-56-1, name is 6-Bromo-1,2,3,4-tetrahydronaphthalene, 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. Safety of 6-Bromo-1,2,3,4-tetrahydronaphthalene

[-BUTYL] lithium (9.6 ml of 2. [5M] solution in hexane) was added [DROPWIS OVER] 30 minutes to a stirred solution of [5-BROM-1,] 2,3, 4-tetrahydronaphthalene in mixture with its regioisomer [6-BROM-1,] 2,3, 4-tetrahydronaphthalene (5 g) in dry THF (125 ml) and hexane (35 ml) [AT-70 C,] stirring was continued at-78 C for 30 minutes, carbon dioxide gas was bubbled through the mixture at-70 C until no further exotherm was evident, carbon dioxide gas addition was continued for a further 10 minutes as the reaction was allowed to warm to ambient temperature, the mixture was poured into 2M aqueous hydrochloric acid (100 ml) and the resulting mixture was extracted with diethyl ether (3 x 50 ml). The combined organic extracts were washed with water (100 ml) and were then extracted with 10% aqueous sodium carbonate solution (3 x 50 ml). The combined aqueous carbonate extracts were acidified carefully by addition of 2M hydrochloric acid to adjust the pH to pH 1. The resulting mixture was extracted with diethyl ether (3 x 50 ml), the combined organic extracts were washed with water (50 ml) and dried [(MGS04)] before solvent was removed by evaporation [IN VACUO TO] give the crude product in 64% yield comprising a mixture [OF REGIOISOMERS] of 5,6, 7,8-tetrahydronaphthalene carboxylic acid. This mixture was purified by repeated recrystallisation from ethyl acetate to give 5,6, 7,8- tetrahydronaphthalene-2-carboxylic acid as crystallised solid in 93% purity along with 5,6, 7, [8-TETRAHYDRONAPHTHALENE-1-CARBOXYLIC] acid as the major component present in the crystallisation mother liquors.

The synthetic route of 6-Bromo-1,2,3,4-tetrahydronaphthalene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2004/792; (2003); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 141215-32-9, A common heterocyclic compound, 141215-32-9, name is 4,7-Dibromobenzo[c][1,2,5]thiadiazole-5,6-diamine, molecular formula is C6H4Br2N4S, 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.

Gas in the flask with argon purged 200mL flask,Added1500mg heterocyclic compound according to Journal (Heterocycles), 1992, Vol. 33, No. 1, p.337-348 method described in the manufacture of 3 (1.54mmol), benzil 325mg (1.54mmol), acetic acid 25mL , the flask was immersed in an oil bath heated to 120 deg.] C, and reacted for 2 hours. Subsequently, the flask was cooled to room temperature (25 deg.] C), the reaction mixture was poured into 300mL of methanol. The solid was recovered by filtration, washed with methanol, and dried under vacuum to give 629mg of the title compound 32 (1.26mmol).

The synthetic route of 141215-32-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sumitomo Chemical Co.,Ltd; Ken, Yoshimura; Kenichiro, Oya; (111 pag.)CN105601662; (2016); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 5279-32-3, 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. 5279-32-3, name is 5,6-Dibromobenzo[d][1,3]dioxole belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A dried round-bottom flask was charged with the correspondingdibromoaryl (16.89 mmol, 1 eq) and furan (84.47 mmol, 5 eq) in dry toluene (50 mL) under argonatmosphere. The solution was cooled at -78 C and n-BuLi 1.6M in THF (18.58 mmol, 1.1 eq) was addeddropwise. After complete addition, the solution was warmed up to -40 C, extracted with EtOAc (3x20mL), dried over magnesium sulfate and concentrated under vacuum. The residue was purified bychormatography column (EtOAc/heptane). From 4,5-dibromoveratrol (5 g), 1.91 g of 1,4-dihydro-6,7-dimethoxy-1,4-epoxynaphthalene (56% yield) were obtained as a white solid (“H-NMR (500 MHz,CDCl3): (ppm) 7.01 (s, 21H), 6.94 (s, 21H), 5.65 (s, 21H), 3.82 (s, 6H)). From 5,6-dibromo-1,3-benzodioxole (4.73 g) were obtained 3.17 g of 5,8-dihydro-5,8-epoxynaphtho[2,3-d][1,3]dioxole (81%yield) as a white solid (“H-NMR (300 MHz, CDCl3): (ppm) 7.07 (s, 2H), 6.86 (s, 2H), 5.96 (d, 1H, J =1.4 Hz), 5.91 (d, 1H, J = 1.4 Hz), 5.66 (s, 2H)).

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, 5,6-Dibromobenzo[d][1,3]dioxole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Deyris, Pierre-Alexandre; Caneque-Cobo, Tatiana; Gomes, Filipe; Narbonne, Vanessa; Maestri, Giovanni; Malacria, Max; Heterocycles; vol. 88; 1; (2014); p. 807 – 815;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 6134-56-1, name is 6-Bromo-1,2,3,4-tetrahydronaphthalene, 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 6134-56-1, Safety of 6-Bromo-1,2,3,4-tetrahydronaphthalene

A mixture of 5-bromo-1,2, 3,4-tetrahydronaphthalene and 6-bromo-1,2, 3,4- tetrahydronaphthalene (20 g), copper [(1)] cyanide (8.6 g) and anhydrous N- methylpyrrolidinone (41.3 g) were stirred under dry nitrogen at [130 C] for 40 h. The mixture was cooled to ambient temperature, further N-methylpyrrolidinone (10 g) was added along with saturated aqueous brine (30 ml), the resulting mixture was stirred at ambient for 3 hours and filtered to remove solids. The filtrates were extracted with n- hexane (3 x 50 ml). The combined organic extracts were washed with water (100 ml), dried [(MGS04)] and evaporated in vacuo to give crude product (16.2 g). This was purified by distillation to give 5,6, 7,8-tetrahydronaphthalene-2-carbonitrile along with regioisomer (13.2 g, 95% purity, 84% yield).

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, 6-Bromo-1,2,3,4-tetrahydronaphthalene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; WO2004/792; (2003); 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. 261723-28-8, name is (3-Bromo-2-fluorophenyl)methanamine, A new synthetic method of this compound is introduced below., COA of Formula: C7H7BrFN

Example 61 1,1-Dimethylethyl [(3-bromo-2-fluorophenyl)methyl]carbamate To a suspension of [(3-bromo-2-fluorophenyl)methyl]amine (5.0 g, 20.3 mmol) and Na2CO3 (5.5 g, 51.9 mmol) in CH2Cl2 (100 mL), the solution of Boc2O (4.5 g, 20.6 mmol) in CH2Cl2 (10 ml) was added dropwise. Then the reaction mixture was stirred overnight at room temperature. After filtration, the solid was washed with CH2Cl2 (50 mL*2), and then the filtrate was washed with water (70 mL*2), brine (70 mL*2) and dried over Na2SO4. After removing the solvent, 5.6 g of 1,1-dimethylethyl [(3-bromo-2-fluorophenyl)methyl]carbamate was obtained (yield: 94%).

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; Glaxo Group Limited; US2009/197871; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 51776-71-7, name is 1-Bromo-4-(difluoromethyl)benzene, molecular formula is C7H5BrF2, 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. Formula: C7H5BrF2

General procedure: Protocol A: The 0.020 M, THF solution obtainedfrom a 0.30 mmol scale preparation of R?CF2 reagent was combined with an electrophile (i.e., substrate) (0.30 mmol) dissolved in 3.0 mE THF at -80 C. The reaction mixture was then allowed to warm to room temperature and allowed to stand for 10 minutes. The solution was poured into saturated NH4C1 in H20 (50 mE) and the organics extracted into DCM (3×50 mE). The organic extract was dried with Mg504, filtered, concentrated onto 3 grams of silica gel, and purified by flash chromatography as specified.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 51776-71-7, its application will become more common.

Reference:
Patent; REGENTS OF THE UNIVERSITY OF MICHIGAN; Szymczak, Nathaniel; Geri, Jacob; US2020/2362; (2020); A1;,
Bromide – Wikipedia,
bromide – Wiktionary