Tag: M.W=200-300

These common heterocyclic compound, 1435-51-4, name is 1,3-Dibromo-5-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. 1435-51-4

9H-pyrido[2,3b]indole (5.04 g, 30.00 mmol, 1.0 eq) was sequentially added to a dry reaction tube with a magnetic rotor.CuI (571.4 mg, 3.00 mmol, 0.01 eq),L-Proline (690.0mg,6.00mmol, 0.02eq) andK2CO3 (8.29 g, 60.00 mmol, 2.0 eq).Pumping nitrogen three times,Then added 1,3-dibromo-5-fluorobenzene (9.14 g, 36.0 mmol, 1.2 eq) andSolvent dimethyl sulfoxide (30 mL).The reaction mixture was placed in an oil bath at 120 C for 1.5 days.Cool to room temperature, add 100 mL of ethyl acetate and dilute with Celite.And fully washed with ethyl acetate, added50mL of water, liquid separation, ethyl acetate extraction of the aqueous phase three times, the organic phase was combined, the organic phase was dried over anhydrous sodium sulfate, filtered, the solvent was evaporated under reduced pressure, the crude product was purified by silica gel column chromatography, eluent (petroleum ether) /methylene chloride = 4:1-2:1),Obtained a white solid 2-Br-F 3.22g,The yield was 31%. The product was used directly in the next step of synthesis.

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 1435-51-4.

Reference:
Patent; Zhejiang University of Technology; Ruisheng Optoelectric Science And Technology (Changzhou) Co., Ltd.; Li Guijie; She Yuanbin; Zhao Xiangdong; Chen Shaohai; (33 pag.)CN108948095; (2018); A;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 22385-77-9 name is 1-Bromo-3,5-di-tert-butylbenzene, 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. 22385-77-9

Preparation 502-(3,5-Di-tert-butylphenyl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolane Bubble nitrogen through DMF (150 mL) for about 15 min prior to adding the reagents. Then dissolve l-bromo-3,5-di-tert-butylbenzene (20.93 g, 77.74 mmol), bis(pinacolato)diboron (22.70 g, 89.40 mmol), and (Iota, – bis(diphenylphosphino)ferrocene)palladium(II) chloride (3.17 g, 3.89 mmol) in the DMF. Stir for 10 min. Add potassium acetate (22.89 g, 233.23 mmol) and bubble argon through the solution for 7 min. Heat the reaction to 85 ¡ãC with stirring for 24 h. Dilute the reaction with water (1.5 L). Collect the resulting brown precipitate by vacuum filtration and washing with water. Dissolve the residue in dichloromethane. Dry this solution over sodium sulfate, filter; collect the filtrate; and concentrate under reducedpressure. Triturate the resulting solids with hot hexanes (400 mL) and filter, washing with hexanes. Concentrate the filtrate to a volume of approximately 300 mL. Place the solution in a freezer overnight. Collect the solid by vacuum filtration and rinsing with cold hexanes. Concentrate the filtrate under reduced pressure to a volume of 150 mL. Cool this mixture in the freezer for about 1.5 h. Collect the resulting solids by vacuum filtration and rinse with cold hexanes. Combine the 2 crops and dry under high vacuum to afford the title compound (21.85 g, 89percent) as a light tan crystalline solid. XH NMR (400 MHz, CDC13) delta 1.33 (s, 12H), 1.33 (s, 18H), 7.53 (t, J = 2.0 Hz, 1H), 7.65 (d, J = 2.0 Hz, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-3,5-di-tert-butylbenzene, and friends who are interested can also refer to it.

Reference:
Patent; ELI LILLY AND COMPANY; BLEISCH, Thomas, John; COATES, David, Andrew; HUGHES, Norman, Earle; JONES, Scott, Alan; NORMAN, Bryan, Hurst; WO2013/66640; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 327-51-5, name is 1,4-Dibromo-2,5-difluorobenzene, 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. 327-51-5

To a -78 C solution of 1 ,4-dibromo-2,5-difluorobenzene (2.72 g, 9.99 mmol) in dry Et20 (30 mL) under an inert atmosphere was added 2.5 M n-butyl lithium solution in hexanes (4 mL, 9.99 mmol) dropwise and the mixture left stirring for 2 h. Crushed CO2 pellets were added slowly and the mixture was allowed to warm to ambient temperature and left stirring for 1 h. After quenching with 1 M aq. HCI (10 mL) the mixture was basified with 1 M aq. NaOH (70 mL) and then washed with Et20 (2 x 50 mL). The aqueous layer was acidified with 1 M aq. HCI (80 mL) and extracted with Et20 (3 x 100 mL). The organic layer was washed with brine (50 mL), dried over Na2S04, filtered and solvent was removed in vacuo to give 4-bromo-2,5- difluoro benzoic acid (2.3 g, 97 %) as an off-white solid, which was used without further purification. SUBSTITUTE SHEET RULE 26 1 H NMR (Method B) (CDC ): delta ppm 9.50 (br s, 1 H), 7.78 (dd, J = 8.2, 6.1 Hz, 1 H), 7.46 (dd, J = 9.3, 5.4 Hz, 1 H); LC-MS (Method C) 234.9/236.9 [M-H]+; RT 3.43 min

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 327-51-5.

Reference:
Patent; REDX PHARMA PLC; HUXLEY, Anthony; KIRK, Ralph; RATCLIFFE, Andrew; LYTH, David; (112 pag.)WO2017/46605; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

941-37-7, The chemical industry reduces the impact on the environment during synthesis 941-37-7, name is 1-Bromo-3,5-dimethyladamantane, I believe this compound will play a more active role in future production and life.

To 100g of 1-bromo-3,5-dimethyl adamantane and 86g of urea, adding 80ml of 80wt% formic acid, heating to 80C and holding for 3 hours. Cooling to the room temperature and adding 95ml of concentrated hydrochloric acid to hydrolyze at 80C for about 1 hour. Adjusting with 30% sodium hydroxide to a pH of 12, extracting with toluene twice, combining the organic layers and washing with water. Concentrating under reduced pressure to yield a limpid yellow solution as the 1-amino-3,5-dimethyl adamantane crude. To the crude, adding 150ml of ethanol and concentrated hydrochloric acid, heating to dissolve and crystallizing to yield white solid. Drying the solid and re-crystallizing with ethanol to yield 61.0g of pure Memantine Hydrochloride. The yield of product is 68.8% (GC 99.5%). 1HNMR (CDCl3, 400MHZ): delta0.833 (6H, singlet), 1.156 (2H, quartet), 1.328 (4H, quartet), 1.683 (4H, quartet), 1.869 (2H, broad signal), 2.179 (1H, broad signal), 8.28(3H, broad signal). MS (Q-Tof micro, ESI+): 179(M+), 164, 122, 108, 93 and 55. Element Analysis (C12H21N.HCl): actual results (calculated value%): C 66.77(66.80), H 10.40(10.28), N 6.48(6.49), Cl 16.39(16.43); To 100g of 1-bromo-3, 5-dimethyl adamantane and 86g of urea, adding 72ml of 94wt% formic acid, heating to 120C and holding for 2 hours. Cooling to the room temperature and adding 385ml of 10% hydrochloric acid to hydrolyze at 100C for about 1 hour. Adjusting with 30% sodium hydroxide solution to a pH of 12, extracting with butyl acetate twice, combining the organic layers and washing with water. Concentrating under reduced pressure to yield a limpid yellow solution as 1-amino-3,5-dimethyl adamantane crude. To the crude, adding 150ml of ethanol and concentrated hydrochloric acid, heating to dissolve and crystallizing to yield white solid. Drying the solid and re-crystallizing with water to yield 60.4g of pure Memantine Hydrochloride. The yield is 68.1 % (GC 99.1 %).

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-3,5-dimethyladamantane. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Shanghai Institute of Pharmaceutical Industry; Zhejiang Kangyu Pharmaceutical Co., Ltd.; EP1674446; (2006); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

327-51-5, 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. 327-51-5, name is 1,4-Dibromo-2,5-difluorobenzene, This compound has unique chemical properties. The synthetic route is as follows.

Into a three-necked flask, to 1,4-dibromo-2,5-difluorobenzene (37.5g, 138.0mmol), 2-nitrophenylboronic acid (23.0g, 138.0mmol), 2M Na2CO3 aqueous solution (138mL, 276mmol), DME (275mL), toluene (275mL), Pd[PPh3]4 (8.0g, 6.9mmol) was added, this mixture was refluxed for 8 hr under Ar atmosphere. After the reaction was cooled to room temperature. The sample was transferred to a separatory funnel, added water (250mL), and extracted with CH2Cl2. After drying with MgSO4, filtered, and concentrated. Purification of a sample was purified by silica gel column chromatography to give a white solid. Yield 26.1g, 60% yield.

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; Idemitsu Kosan Corporation; Kato, Tomoki; Numata, Masaki; Yoshida, K.; Nishimura, Kazuki; Eiwakuma, Toshihiro; Hosokawa, Chisio; (108 pag.)KR101500796; (2015); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

327-75-3, A common heterocyclic compound, 327-75-3, name is 1-Bromo-2,4-bis(trifluoromethyl)benzene, molecular formula is C8H3BrF6, 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 stirred solution of 3-methyl-4-nitro-lH-pyrazole (869 mg, 0.068 mmol, 1 equiv) l-bromo-2,4-bis(trifluoromethyl)benzene (2 g, 0.068 mmoles, leq) in DMF (20 mL) was added K CO (1.89 g, 0.0136 mmol, 2 equiv) and the reaction mixture was stirred for 15 minutes. Cul (0.026 g, 0.2eq, O.OOlmoles) and L-proline (0.317 g, 0.02 mmol, 0.4 equiv.) were added to the reaction mixture. The reaction mixture was allowed to stir for 24 hour at 100 C. Product formation was confirmed by LCMS. After completion of reaction, reaction mixture was diluted with water and extracted with ethyl acetate (3×100 mL). Combined organic extracts were washed with water (4×100 mL), dried over anhydrous NaSCL and concentrated under reduced pressure to obtain which was purified by flash chromatography (EtOAc/ Hexane) to obtain titile compound l-(2,4-bis(trifluoromethyl)phenyl)-3-methyl-4- nitro-lH-pyrazole (1.0 g). LCMS 339 [M+H] +.

The synthetic route of 1-Bromo-2,4-bis(trifluoromethyl)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PRAXIS BIOTECH LLC; ALFARO, Jennifer; BELMAR, Sebastian; NUNEZ VASQUEZ, Gonzalo Esteban; PUJALA, Brahmam; SATHE, Balaji Dashrath; BERNALES, Sebastian; CHAKRAVARTY, Sarvajit; THAKRAL, Pooja; PATIDAR, Rajesh Kumar; (344 pag.)WO2019/195810; (2019); A2;,
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. 82842-52-2, name is 3-Bromo-2,4,6-trimethylaniline, This compound has unique chemical properties. The synthetic route is as follows., 82842-52-2

(B) 2,2′-[[2-[(3-bromo-2,4,6-trimethylphenyl)amino]-2-oxoethyl]]imino]bisacetic acid A suspension of 9.56 g of nitrilotriacetic acid in pyridine (dried over molecular sieves) is prepared with the exclusion of moisture (CaSO4 drying tube) and heated to 50 C. Acetic anhydride (5.11 g) is added dropwise. The reaction mixture clears and is heated to 100 C. After maintaining the temperature for 40 minutes, the reaction mixture is cooled to 55 C. and a solution of 10.7 g 3-bromo-2,4,6-trimethylaniline in 25 ml of dry pyridine is added slowly. The reaction is heated to 100 C. and after 1.5 hours at this temperature, the solution is cooled in an ice-bath. The reaction mixture is rotary evaporated to a semisolid which is dissolved in 125 ml of 10% sodium hydroxide w/v. The basic layer is then extracted with two 100 ml portions of methylene chloride. Distilled water (100 ml) is added to the basic layer which is then brought to pH 3 with concentrated hydrochloric acid to give a precipitate. After refrigeration for about 16 hours, the crude product is filtered, washed with cold distilled water and dried under vacuum at 40 C. The crude product is dissolved in 100 ml of 60% aqueous ethanol, treated with 3.0 g of Darco and filtered hot through a Hyflo-bed to give a solution. Crystals precipitate and are filtered, washed with three 25 ml portions of 50% aqueous ethanol and dried under vacuum at 40 C. The reaction yields 9.1 g of the title compound, melting point 198-200 C., dec.

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; E. R. Squibb & Sons, Inc.; US4418208; (1983); A;,
Bromide – Wikipedia,
bromide – Wiktionary

73918-56-6, Adding some certain compound to certain chemical reactions, such as: 73918-56-6, name is 2-(4-Bromophenyl)ethanamine, 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 73918-56-6.

General procedure: The appropriate aldehyde 6a-c and 12a-g (1 mmol) was dissolved in 5 mL of CH2Cl2 in a round bottom flask. Then AcOH (1 mmol) and the appropriate amine (1.1 mmol) were added to the stirring solution at room temperature. The mixture was allowed to stir at room temperature for 20 min before NaBH(AcO)3 (3 mmol) was added. The mixture was allowed to stir at room temperature for overnight. Then,after completion, the reaction was quenched with NaOH 1M solution(15 mL). The mixture was then allowed to stir for 30 min. The reaction mixture was then diluted with EtOAc (10 mL), washed two times with EtOAc (10 mL) and once with brine (20 mL). The organic extracts were collected and then dried over Na2SO4, and the solvent was evaporated to yield the crude compounds 7a-e, 13a-o, 14a-b and 15a which were purified by silica gel column chromatography.

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 73918-56-6.

Reference:
Article; Liu, Pingxian; Yang, Yang; Ju, Yuan; Tang, Yunxiang; Sang, Zitai; Chen, Lijuan; Yang, Tao; An, Qi; Zhang, Tianyu; Luo, Youfu; Bioorganic Chemistry; vol. 80; (2018); p. 422 – 432;,
Bromide – Wikipedia,
bromide – Wiktionary

3972-65-4, name is 1-Bromo-4-(tert-butyl)benzene, 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. 3972-65-4

In a J.T. Young tube, 0.75 mmol of olefinic compound, 0.5 mmol of aryl halide, 0.6 mmol of potassium carbonate, 0.005 mmol of triphenylphosphite, 0.0005 mmol of Pd(dba)2 or the respective palladium source, and 0.1 mmol of trans-stilbene (as internal standard) were dissolved in 1 mL of DMF under nitrogen atmosphere. The tube was sealed and before putting it into a 100 C hot bath of silicon oil, it was purged three times carrying out cycles of vacuum/nitrogen. After 20 h of continuous stirring the mixture was cooled to room temperature and 0.5 mL of 2 M HCl and 0.5 mL ofdichloromethane were added. The organic phase was analyzed by GC. The products were crystallized from methanol/dichloromethane cold mixtures and characterized by 1H NMR, GC-MS, IR, and mp and compared with the reported spectra.

Statistics shows that 3972-65-4 is playing an increasingly important role. we look forward to future research findings about 1-Bromo-4-(tert-butyl)benzene.

Reference:
Article; Cardenas, Juan C.; Fadini, Luca; Sierra, Cesar A.; Tetrahedron Letters; vol. 51; 52; (2010); p. 6867 – 6870;,
Bromide – Wikipedia,
bromide – Wiktionary

327-51-5, 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. 327-51-5, name is 1,4-Dibromo-2,5-difluorobenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Into a three-necked flask, 1,4-dibromo-2,5-difluorobenzene (5.4g, 20.0mmol), compound 27 (16.1g, 42.0mmol), 2M Na2CO3 aqueous solution (40mL, 80.0mmol), DME (40mL), toluene (40mL ), Pd[PPh3]4 (1.2g, 1.0mmol) were mixed, this mixture was refluxed for 8 hr under Ar atmosphere. After the reaction was cooled to room temperature. The sample was transferred to a separatory funnel, added water (100mL), extracted with CH2Cl2 and dried in. MgSO4, filtered, and concentrated. Purifying the sample by silica gel column chromatography to obtain a white solid. Yield 11.8g, 75% yield

The synthetic route of 327-51-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Idemitsu Kosan Corporation; Kato, Tomoki; Numata, Masaki; Yoshida, K.; Nishimura, Kazuki; Eiwakuma, Toshihiro; Hosokawa, Chisio; (108 pag.)KR101500796; (2015); B1;,
Bromide – Wikipedia,
bromide – Wiktionary