Month: March 2021

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. 51376-06-8, name is 5-Bromobenzo[c][1,2,5]oxadiazole, This compound has unique chemical properties. The synthetic route is as follows., Formula: C6H3BrN2O

5-Brorno-2,l,3-benzoxadiazole (5.5 g, 27.6 mmol)), potassium vinylfluoroborate (7.40 g, 55.3 mmol), and PdC12(dppi>;CH2C12Adduct (1.088 g, 1.332 mmol) were suspended in ethanol (75 ml) then added TEA (7.70 ml, 55.3 mmol). The reaction mixture was then degassed and heated to reflux for 3hrs. The reaction was diluted with ethyl acetate and washed with brine. The organic layer was dried over Na2SO4, filtered and evaporated to dryness. The residue was purified through a 330g ISCO Redi-Sep silica gel plug and eluted with 20%ETOAc/hexane to yield 5- ethenyl-2 , 1 , 3 -benzoxadiazole.1H-NMR (600 MHz5 CDCl3): delta ppm 7.81(d, J=9.3 Hz, IH), 7.66 (s, IH), 7.63 (d, J-9.3 Hz, IHX 6.35 (d, J=10.9 Hz, 0.5H), 6.80 (d, J-10.9 Hz, 0.5H)s 5.94 (d. J-17.5 Hz, IH)5 5.55 (d, J= H Hz5 IH).

According to the analysis of related databases, 51376-06-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP &; DOHME CORP.; PASTERNAK, Alexander; SHAHRIPOUR, Aurash; TANG, Haifeng; TEUMELSAN, Nardos, H.; YANG, Lihu; ZHU, Yuping; WALSH, Shawn, P.; WO2010/129379; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 58971-11-2, These common heterocyclic compound, 58971-11-2, name is 3-Bromophenethylamine, 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.

A mixture of intermediate I-60 (8.0 g, 40 mmol, 1.0 eq) and 2,6-lutidine(4.8 mL, 41 mmol, 1.03 eq) in dry dichloromethane (160 mL) was cooled to 0 C. and neat TFAA (5.6 mL, 39.6 mmol, 0.99 eq) was added drop wise. The reaction mixture was warmed to room temperature and stirred for 16 hours. Water (150 mL) was added, the aqueous layer was extracted with dichloromethane and the combined organic layers were washed with aqueous HCl (1.0 M in water) and a saturated aqueous solution of NaHCO3. The combined organic layers were dried over anhydrous Na2SO4, the solids were removed by filtration and the filtrate was concentrated by evaporation to give intermediate I-61 (11 g, 92%). 1H-NMR (400 MHz, CDCl3) delta: delta 7.40 (d, 1H, J=8.0 Hz), 7.35 (t, 1H, J=1.6 Hz), 7.20 (t, 1H, J=7.6 Hz), 7.12 (d, 1H, J=8.0 Hz), 6.55 (brs, 1H), 3.59 (q, 2H, J1=6.4 Hz, J2=13.2 Hz), 2.86 (t, 2H, J=6.8 Hz). MS (ESI): m/z 296 (M+H+).

Statistics shows that 3-Bromophenethylamine is playing an increasingly important role. we look forward to future research findings about 58971-11-2.

Reference:
Patent; Chytil, Milan; Engel, Sharon R.; Fang, Qun Kevin; Spear, Kerry L.; US2010/204214; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 16518-62-0, name is 3-Bromo-N,N-dimethylaniline, 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 16518-62-0, Recommanded Product: 16518-62-0

Step A: bis-(3-dimethylaminophenyl)amine Under dinitrogen atmosphere, 1 equivalent of 3-bromo-N,N-dimethylaniline (1 g), 1.5 equivalent of sodium tert-butylate (0.721 g), 0.1 equivalent of Pd(dba)2 (0.288 g), 0.12 equivalent of dppf (0.555 g) and 20 mL of toluene are introduced into a flask. The flask is fitted with a PTFE septum and 1.2 equivalent of N,N-dimethylbenzene-1,3-diamine (0.817 g) is added thereto using a syringe. The reaction medium is heated at 90¡ã C. for 12 hours, thereafter is cooled to room temperature and concentrated under reduced pressure. The product is purified by flash chromatography using a gradient of 5percent to 12percent of ethyl acetate in hexane (Rf: 0.33) to give 0.963 g of the expected product with a yield of 75percent.NMR 1H: (CDCl3) 7.13 (t, 2H), 6.5 (d, 2H), 6.49 (d, 2H), 6.38-6.36 (m, 2H), 5.68 (s large, 1H), 2.95 (s, 12H).MS (M+1): 256

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, 3-Bromo-N,N-dimethylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PHARMA HYDRO DEVELOPMENT – P.H.D.; US2010/204215; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

50548-45-3, name is 1-Bromodibenzo[b,d]furan, 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. Safety of 1-Bromodibenzo[b,d]furan

(4) In a 1L reaction flask, add intermediate c (51.65 g, 100 mmol), 9-phenyl-9H-carbazole-2-amine (25.83 g, 100 mmol), and tris (dibenzylideneacetone) diamine. Palladium (2.75g, 3mmol), tri-tert-butylphosphine (1.21g, 6mmol), sodium tert-butoxide (19.22g, 200mmol), 500ml of toluene, heated to 110 C for 12h under a nitrogen atmosphere, and monitored by liquid phase After the reaction is completed, the temperature is lowered, 1-bromodibenzofuran (24.71 g, 100 mmol) is added, the temperature is raised to 110 C and the reaction is continued for 8 hours. The reaction is monitored by liquid phase, cooled to room temperature, washed with water, filtered, ethyl acetate, dried, 54.18 g of intermediate e can be obtained with a yield of 63%.

The synthetic route of 50548-45-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wuhan Shang Sai Optoelectric Technology Co., Ltd.; Mu Guangyuan; Zhuang Shaoqing; Ren Chunting; (31 pag.)CN110372570; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 16657-07-1,Some common heterocyclic compound, 16657-07-1, name is 7-Bromo-1H-indene, molecular formula is C9H7Br, 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) Synthesis of 7-isopropylindene Using a 300 ml three-necked flask as the reactor, under a nitrogen stream, 1.36 g (2.57 millimoles) of [1,2-bis (diphenylphosphino)ethane]dichloronickel(II) was dissolved in 20 ml of tetrahydrofuran. To this suspension there was added a solution of 10 g (51.30 millimoles) of 7-bromoindene in 100 ml of tetrahydrofuran, prepared based on the method described in J. Org. Chem. 49, 4226-4237(1984). After dropwise addition of 51 ml (102.60 millimoles) of isopropylmagnesium bromide (2N) to the mixed solution while cooling on ice, the mixture was heated to reflux for 20 hours. After reflux, hydrolysis was performed with a saturated aqueous solution of ammonium chloride, distilled water was added, extraction was performed several times with diethyl ether, and then the extract was washed once with saturated saline and dried over anhydrous magnesium sulfate. After drying, the magnesium sulfate was filtered off and the solvent was purified with a silica gel column to obtain 7.14 g of 7-isopropylindene as a yellow oil (88% yield).

The synthetic route of 16657-07-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chisso Petrochemical Corporation; US2003/149200; (2003); 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. 10269-01-9, name is (3-Bromophenyl)methanamine, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 10269-01-9

General procedure: A mixture of 0.55mmol of 8-bromo-7-(2-bromoethyl)theophylline 7a or 8-bromo-7-(3-chloropropyl)theophylline 7b or 8-bromo-7-(4-bromobutyl)theophylline 7c, 1.1mmol of appropriate aromatic amine, 1,6 mmol of TEBA and 1.00ml of propanol was heated in closed vessels in microwave oven (300 Watt, Power Max Off, 160C, 10bar) for 1h. The solvent was removed and the residue was treated with ethanol. The products were purified by crystallization from ethanol or flash column chromatography over silica gel with CH2Cl2 : MeOH (100 : 0 to 80 : 20). The precipitate was filtered off and dried.

According to the analysis of related databases, 10269-01-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Za?uski, Micha?; Schabikowski, Jakub; Schlenk, Miriam; Olejarz-Maciej, Agnieszka; Kubas, Bart?omiej; Karcz, Tadeusz; Kuder, Kamil; Latacz, Gniewomir; Zygmunt, Ma?gorzata; Synak, David; Hinz, Sonja; Mueller, Christa E.; Kie?-Kononowicz, Katarzyna; Bioorganic and Medicinal Chemistry; vol. 27; 7; (2019); p. 1195 – 1210;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 21524-34-5,Some common heterocyclic compound, 21524-34-5, name is 2-Bromo-1,3,5-triisopropylbenzene, molecular formula is C15H23Br, 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: An oven-dried, resealable Schlenk tube containing a stirbar was charged with aryl halide (1.0 mmol), ketone (1.1 mmol), potassium tert-butoxide (1.5 mmol), and 1 mol % catalyst, and backfilled with nitrogen. Toluene (1.5 mL) was sequentially injected, and the mixture was stirred in an oil bath at reflux temperature for the time specified. After the reaction was completed, the reaction mixture was filtered by chromatographed on silica gel and washed with EtOAc. The filtrate was dried over MgSO4 and filtered before the solvent was removed on a rotary evaporator. The pure product was obtained by preparative TLC and the yield was calculated based on ArX (the purified products were identified by comparison of melting points with the literature data or by 1H NMR and 13C NMR spectra. New compounds were determined by HRMS spectra).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-1,3,5-triisopropylbenzene, its application will become more common.

Reference:
Article; Zhang, Jinli; Yang, Xueqian; Cui, Xiuling; Wu, Yangjie; Tetrahedron; vol. 67; 45; (2011); p. 8800 – 8807;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 69321-60-4, 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. 69321-60-4, name is 2,6-Dibromotoluene, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 1,3-dibromo-2-methylbenzene (Combi Blocks catOT-1437: 339 mg, 1.356 mmol), tert-butyl 2-(2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-4,6-dihydro-5H-pyrrolo[3,4-d]thiazole-5-carboxylate (200.0 mg, 0.452 mmol), sodium carbonate (96 mg, 0.904 mmol) and tetrakis(triphenylphosphine)palladium(0) (52.2 mg, 0.045 mmol) in dioxane (3.00 mL)/ water (1.0 mL) was heated at 90 C. overnight. The reaction was then cooled to room temperature, diluted with saturated aqueous NH4Cl, and extracted with EtOAc (3¡Á30 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and the filtrate was concentrated under reduced pressure. The crude residue was purified by chromatography on silica gel, eluting with 0-40% EtOAc/hexanes, to give the desired product (210 mg). LC-MS calculated for C24H26BrN2O2S (M+H)+: m/z=485.1/487.1; found 485.0/487.0.

The chemical industry reduces the impact on the environment during synthesis 2,6-Dibromotoluene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Incyte Corporation; Wu, Liangxing; Qian, Ding-Quan; Lu, Liang; Lajkiewicz, Neil; Konkol, Leah C.; Li, Zhenwu; Zhang, Fenglei; Li, Jingwei; Wang, Haisheng; Xu, Meizhong; Xiao, Kaijiong; Yao, Wenqing; (101 pag.)US2018/177784; (2018); 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. 2789-89-1, name is 1,2-Bis(4-bromophenyl)ethyne, A new synthetic method of this compound is introduced below., HPLC of Formula: C14H8Br2

To a 13 ¡Á 150 mm test tube equipped with magnetic stir bar were added [RhCp*(CH3CN)3](SbF6)2 (6.6mg, 4 mol %), NaOAc (32.8mg, 0.4 mmol, 2 equiv) and 2a-2o (0.3 mmol, 1.5 equiv). The test tube was sealed with a rubber septum and removed from the glove-box. The solution of 1a-1r (0.2 mmol, 1 equiv)in EtOH (2 mL) was injected into the test tube via syringe. The reaction mixture was placed in a preheated oil bath (60 ) for 12 h. Then the reaction mixture was concentrated in vacuo, the residue was dissolved in methylene chloride and purified by column chromatography (silica gel, n-hexane/EtOAc =20/1). 1-Methyl-3,4-diphenylisoquinoline (3aa): The title compound was obtained as white crystal in 91% yield (54.2 mg). 1H NMR (400 MHz, CDCl3) delta 8.24 – 8.16(m, 1H), 7.66 (m, 1H), 7.63 – 7.55 (m, 2H), 7.41 – 7.28 (m, 5H), 7.26 – 7.12 (m,5H), 3.09 (s, 3H). 13C NMR (101 MHz, CDCl3) delta 157.78, 149.37, 140.90, 137.56,136.06, 131.44, 130.32, 130.04, 129.29, 128.24, 127.66, 127.18, 127.01, 126.62,126.29, 126.19, 125.60, 22.73. HRMS (EI) calcd. for C22H17N: [M]+, 295.1361. Found: m/z 295.1358.

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:
Article; Chu, Benfa; Fang, Lili; Guo, Shan; Qi, Bing; Shi, Pengfei; Wang, Qi; Zhu, Jin; Tetrahedron Letters; (2020);,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 67567-26-4, 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 67567-26-4 as follows.

To 4-bromo-2,6-difluoroaniline (1.0 g, 4.81 mmol) and copper (I) cyanide (1.28 g, 14.3 mmol) was added DMF (10 mL) under nitrogen and the resulting mixture was heated at 160 C for 18 h. After 18 h, the mixture was cooled, poured onto a 12% aqueous ammonia solution and extracted with EtOAc (2X). The combined organic extract was washed with water. The organic phase was combined with a little water and was filtered through celite to remove suspended solids. The organic phase was then separated from the water, then washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification by flash chromatography (12% EtOAc/ hexanes eluent) provided 4-amino-3,5-difluorobenzonitrile as a white solid. 1H NMR (300 MHz, Chloroform-d) delta 7.19 – 7.14 (m, 2H), 4.29 (br. s, 2H).

According to the analysis of related databases, 67567-26-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UNIVERSITY OF HAWAII; TURKSON, James; YUE, Peibin; TIUS, Marcus; BROTHERTON-PLEISS, Christine; LOPEZ TAPIA, Francisco, Javier; (420 pag.)WO2018/136935; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary