Month: December 2020

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 55289-36-6 as follows. 55289-36-6

General procedure: To a cooled solution of the chosen 2-methylaniline dissolved in HBF4 (50% solution in water; 15-30 mL) was added at 0 C dropwise a cooled aqueous solution of NaNO2 (1 equiv in the minimum of water). After the end of the addition, the mixture was stirred 1 h at 0 C and 2 h at room temperature. Then, the resulting precipitate was filtered, washed with Et2O (3 ¡Á 100 mL) and dried to obtain the corresponding 2-methylphenyldiazonium tetrafluoroborate salts which were directly added in one portion under nitrogen to a stirred mixture of KOAc (2 equiv) and 18-crown-6 (0.05 equiv) in dry CHCl3 (350-700 mL). After 2 h at room temperature, the mixture was filtered, washed with CHCl3 (3 ¡Á 100 mL) and the organic filtrate was finally concentrated in vacuo. The residual gum was purified by column chromatography on silica gel (EtOAc/cyclohexane 1:3) to give the desired indazoles 1 and 2a.

According to the analysis of related databases, 55289-36-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Lohou, Elodie; Sopkova-De Oliveira Santos, Jana; Schumann-Bard, Pascale; Boulouard, Michel; Stiebing, Silvia; Rault, Sylvain; Collot, Valerie; Bioorganic and Medicinal Chemistry; vol. 20; 17; (2012); p. 5296 – 5304;,
Bromide – Wikipedia,
bromide – Wiktionary

553-94-6,Some common heterocyclic compound, 553-94-6, name is 2,5-Dimethylbromobenzene, molecular formula is C8H9Br, 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: In a typical run, in the air atmosphere, a reaction tube was charged with aryl halide (1.0 mmol), phenylboronic acid (1.0 mmol), ionic Pd-NHC complex (0.001 mmol), and K2 CO3 (1 mmol). Solvent (2-propanol/H2 O, 1:2 v/v) (3 mL) was added to tube and the mixture was vigorously stirred at room temperature for a specific time. After the desired reaction time, 5 mL of diethyl ether was added to the reaction mixture, and the organic phase was extracted with the appropriate volume of water and dried over MgSO4 . Next, the organic phase (1 L ) was injected to GC. The reactions were monitored with a Shimadzu GC-2010 Plus (FID) (Kyoto, Japan). The results were the average of the 2 runs. The yields were determined by GC with use of undecane as the internal standard. All of the coupling products were previously reported. The turn over frequency (TOF) was calculated using the following equations: TOF = TON/time of reaction and TON = moles of desired product formed/moles of the catalyst.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,5-Dimethylbromobenzene, its application will become more common.

Reference:
Article; Ya?ar, Sedat; Akkoc, Mitat; Oezdemir, Nam?k; Oezdemir, ?smail; Turkish Journal of Chemistry; vol. 43; 6; (2019); p. 1622 – 1633;,
Bromide – Wikipedia,
bromide – Wiktionary

68322-84-9, Adding a certain compound to certain chemical reactions, such as: 68322-84-9, name is 2-Bromo-1-fluoro-4-(trifluoromethyl)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 68322-84-9.

EXAMPLE 4 4-Trifluoromethyl-10-aza-tricyclo[6.3.1.02,7]-dodeca-2(7),3,5-triene Hydrochloride (See Grunewald, G. L.; Paradkar, V. M.; Pazhenchevsky, B.; Pleiss, M. A.; Sall, D. J.; Seibel, W. L.; Reitz, T. J. J. Org. Chem. 1983, 48, 2321-2327. Grunewald, G. L.; Markovich, K. M.; Sall, D. J. J. Med. Chem. 1987, 30, 2191-2208.) The title compound was prepared by the methods described in Examples 1 and 2 starting with 2-fluoro-5-trifluoromethylbromobenzene. 1H NMR (400 MHz, CD3OD) delta 7.71 (s, 1H), 7.64 (d, J=8.0 Hz, 1H), 7.57 (d, J=8.0 Hz, 1H), 3.46 (m, 4H), 3.21 (d, J=12.5 Hz, 2H), 2.41 (m, 1H), 2.16 (d, J=11.5 Hz, 1H). APCI MS m/e 228.2 [(M+1)+]. (HCl salt) M.p. 244-246 C. Anal. Calcd. for C12H12F3N.HCl.1/3H2O: C, 53.44; H, 5.11; N, 5.19. Found C, 53.77; H, 4.82; N, 5.18.

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-1-fluoro-4-(trifluoromethyl)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Pfizer Inc; US6605610; (2003); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding some certain compound to certain chemical reactions, such as: 461-96-1, name is 1-Bromo-3,5-difluorobenzene, 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 461-96-1. 461-96-1

Under a nitrogen atmosphere, 2,2,6,6-tetramethylpiperidine (7.3 g) was dissolved in THF (30 mL) and cooled to -70 C. or lower.To the solution, a 1.6 M butyl lithium / hexane solution (32 mL) was added dropwise at a rate such that the internal temperature did not reach -65 C. and then stirred at -70 C. or lower for 30 min.Subsequently, a solution prepared by dissolving 3,5-difluorobromobenzene (10 g) in THF (50 mL) was added dropwise to the stirring reaction solution at a rate such that the internal temperature did not exceed -65 C., At room temperature for 1 hour to prepare phenyllithiums.In a separate reaction vessel, difluorodibromomethane (16.3 g) was dissolved in THF (160 mL)The dissolved solution was cooled to -70 C. or lower, and a solution of phenyllithium prepared in advance was added to the solution using a cannula, followed by stirring at -70 C. or lower for 1 hour, then cooled to room temperature .Water and hexane were added to the reaction solution to separate the organic layer, and the organic layer was washed twice with saturated brine.Sodium sulfate was added to the organic layer after washing and dried, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 4-bromo-2,6-difluoro- (bromodifluoromethyl) benzene and 1,4 – dibromo-2,6-difluorobenzene (13.7 g).When the ratio of each compound in the mixture was measured by gas chromatography,81.6% of 4-bromo-2,6-difluoro- (bromodifluoromethyl) benzene and 18.4% of 1,4-dibromo-2,6-difluorobenzene.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1-Bromo-3,5-difluorobenzene.

Reference:
Patent; DIC Corporation; Tojo, Kenta; Kusumoto, Tetsuo; Takatsu, Haruyoshi; (11 pag.)JP6047884; (2016); B2;,
Bromide – Wikipedia,
bromide – Wiktionary

615-54-3, 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. 615-54-3, name is 1,2,4-Tribromobenzene, A new synthetic method of this compound is introduced below.

Under an argon stream, 1.50 g (6.02 mmol) of 4- (2-quinolyl) phenylboronic acid,542 mg (1.72 mmol) of 1,2,4-tribromobenzene,159 mg (0.138 mmol) of tetrakis (triphenylphosphine) palladium,And 7.74 mL (7.74 mmol) of 1 M potassium carbonate aqueous solution were dissolved in 60 mL of dioxane,And the mixture was heated and stirred at 100 C.After cooling to room temperature, 500 mL of pure water was added and the mixture was separated and extracted with chloroform.After distilling off the solvent under reduced pressure, the obtained crude product was recrystallized twice using toluene as a solvent,Objective4,4 ” – di (2-quinolyl) -4 ‘- [4- (2-quinolyl) phenyl] -1,1’: 2 ‘, 1 “Of a white solid (yield 680 mg, yield 57.5%).

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; TOSOH CORPORATION; FUJITA, KANA; ARAI, NOBUMICHI; NOMURA, KEISUKE; IIDA, TAKASHI; TANAKA, TSUYOSHI; (76 pag.)JP6264877; (2018); B2;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 55289-36-6, name is 3-Bromo-2-methylaniline, molecular formula is C7H8BrN, 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. 55289-36-6

To a solution of compound 298a (8g, 43mmol) in dichloromethane (80ml) at 0 C was added compound 298b (16ml, 113.5mmol). The reaction solution was stirred at 0 C for 30 minutes, and then solid potassium nitrate (5.43g, 53.7 mmol), the ice bath was removed, and the reaction solution was stirred at room temperature for 4 hours. LCMS monitored the reaction of the raw materials. The reaction solution was concentrated and dried under vacuum. The residue was added with water and extracted twice with dichloromethane (2 * 200 ml). The organic phases were combined, dried over anhydrous sodium sulfate, and filtered with suction.It was dried and the crude product was passed through the column to obtain a yellow solid compound (Example 298c, 4.0972g, yield 28.57%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 55289-36-6, its application will become more common.

Reference:
Patent; Jiaxing Tekeluo Biological Technology Co., Ltd.; Xing Li; Li Guanqun; Wang Xiaolei; Cai Yuting; Jiang Xiang; Pan Xiang; Zhu Wenhao; Wang Yang; Wang Zengquan; (83 pag.)CN110627775; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

39478-78-9, name is 5-Bromo-2-methylaniline, 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. 39478-78-9

General procedure: An equimolar mixture of isatin/5-bromoisatin and an aromatic primary amine were introduced into an Erlenmeyer flask. Ethanol (1 mL) and a few drops of acetic acid were added. The Erlenmeyer flask was placed in an ultrasonic bath filled with water (80 Hz,100%), the temperature was adjusted at 40C. At the end of the reaction (monitored by TLC), the product obtained by filtration was recrystallized from ethanol. For the reactions carried out in microwave Biotage, the reagents in 4 mL of ethanol were put in a magnetic stir bar for 2-5 mL vial and the temperature was set at 150C, 160C then 180C.

Statistics shows that 39478-78-9 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-2-methylaniline.

Reference:
Article; Chemchem, Meryem; Menacer, Rafik; Merabet, Naima; Bouridane, Hamida; Yahiaoui, Samir; Moussaoui, Sadjia; Belkhiri, Lotfi; Journal of Molecular Structure; vol. 1208; (2020);,
Bromide – Wikipedia,
bromide – Wiktionary

52997-43-0, 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 52997-43-0 as follows.

Under nitrogen protection, nitrogen is protected. The intermediate product 1, 2 – bis (4 -hydroxyphenyl) ethane -1, 2 – diketone (2g, 8.26 mmol), potassium carbonate (2.4g, 0.2 mmol), tetrabutylammonium bromide (1.33g, 4.13 mmol) were dissolved in N 70 ml) solutions, followed by 60 C stirring 1h, followed by 7 – (bromomethyl) pentadecane (4.04g, 13.2 mmol), 120 C and refluxing 24h out unitunit_ type. After completion of the reaction, the reaction was completed. The reaction solution was cooled to room temperature, and saturated 200 ml brine and dichloromethane were added thereto to extract, and the organic phase, dried over anhydrous magnesium sulfate, concentrated, and then subjected to column chromatography separation and purification. The eluate containing the objective compound was collected by column 300 – 400 silica gel as a 1:3 stationary phase, eluting, with a dichloromethane/petroleum ether volume ratio timetime mixture and dried, yielding a yellow powdery intermediate product 1, 2 – bis (4 – (hexadecyloxy) phenyl) ethane -1, was obtained. 2 – Diketone 3.05g, yield=unitz 45.4%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 52997-43-0, and friends who are interested can also refer to it.

Reference:
Patent; Zhejiang University of Technology; Lv Xiaojing; Bi Qian; Ouyang Mi; Qian Liang; Xu Xinjia; Zha Lixia; (13 pag.)CN110066287; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

24358-62-1,Some common heterocyclic compound, 24358-62-1, name is 1-(4-Bromophenyl)ethylamine, molecular formula is C8H10BrN, 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.

A solution of 4-bromo-a-methylbenzylamine (6.57 mmol) and N,N-diisopropylethylamine (9.85 mmol) in anhydous THF (30 mL) and 2-methoxybenzoyl chloride (7.22 mmol) at 0 C was then allowed to return to RT and stirred for 15 h. The mixture was quenched with a saturated solution of ammonimum chloride (40 mL), extracted with EtOAc (3×20 mL). The combined organic extracts were washed with water (2×30 mL), a saturated solution of brine (30 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. Further purification gave the titled compound (6.19 mmol) as a white solid. UPLC-MS (ES, Short acidic): 1 .96 mi m/z 336.1 [M+2]

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-(4-Bromophenyl)ethylamine, its application will become more common.

Reference:
Patent; REDX PHARMA PLC; GUISOT, Nicolas; (266 pag.)WO2017/103611; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

937046-98-5, 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. 937046-98-5 name is 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine, 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.

To a solution of [3-(4,4,5,5-tetramethyl-[1,3,2]ciioxaborolan-2-yl)-benzyl]-carbamic acid tert-butyl ester (7 g, 21 mmol) in DME (100 mL), 7-bromo-pyrro]o[2,1-f][1 ,2,4]triazin-4- ylamine (2.5 g, 11.7 mmol), PdCI2(dppf) complexed with CH2CI2 (850 mg, 1.2 mmol) and 2 N Na2CO3 (12 mL) were added. The mixture was degassed for 20 min and was then heated to 80 0C for 23 hours. After cooling, the mixture was partitioned between EtOAc and H2O, and the organic layer was separated and dried. Biotage chromatography (50- 100% EtOAc) provided the title product as off white solid 2.6 g (76%). 1H NMR (300 MHz, DMSO-cfe) 57.80-7.50 (m, 6 H), 7.20-7.0 (m, 3 H), 4.80 (s, 2 H), 1.30 (s, 9 H); ES- MS m/z 339 [M+H]+, HPLC RT (min) 2.41.

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; BAYER PHARMACEUTICALS CORPORATION; WO2007/56170; (2007); A2;,
Bromide – Wikipedia,
bromide – Wiktionary