Category: 10040-96-7

Some common heterocyclic compound, 10040-96-7, name is 1-(4-Bromophenyl)imidazole, molecular formula is C9H7BrN2, 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. Application In Synthesis of 1-(4-Bromophenyl)imidazole

General procedure: To a solution of 1-(4-bromophenyl)-N, N-dimethylmethanamine (23.2 mg,0.108 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos)(10.4 mg, 0.018 mmol) and tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3) (8.3mg, 9.6 mumol) in 1,4-dioxane (1 ml) were added to compound 5(38.2 mg, 0.090 mmol) and N,N-diisopropylethylamine (31.4 mul, 0.180 mmol)and refluxed for 3 h. The mixture was filtrated by either Chromatodisc(0.45 mum) (KURABO INDUSTRIES, Osaka, Japan) or celite. The filtered solidwere washed with MeOH three times and then the assembled solution wasconcentrated under reduced pressure. The resulting residue was purified bypreparative TLC (CHCl3/MeOH/28% aq. NH4OH=10/1/0.1) to obtain thetitle compound as an off-white solid

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 10040-96-7, its application will become more common.

Reference:
Article; Wakiyama, Yoshinari; Kumura, Ko; Umemura, Eijiro; Masaki, Satomi; Ueda, Kazutaka; Sato, Yasuo; Watanabe, Takashi; Hirai, Yoko; Ajito, Keiichi; Journal of Antibiotics; vol. 70; 1; (2017); p. 52 – 64;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 10040-96-7, 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. 10040-96-7, name is 1-(4-Bromophenyl)imidazole, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 21 (0.212 g, 1.12 mmol), CuI (20 mg, 0.112 mmol), (PPh3)2PdCl2 (40 mg, 0.056 mmol) and triethylamine (0.23 mL, 1.68 mmol) in acetonitrile (10 mL) was added 1-(4-bromophenyl)imidazole (0.5 g, 2.24 mmol). The reaction mixture was recharged with argon and stirred at 80 C for 3 h in a sealed tube. The mixture was extracted with ethyl acetate and the organic layer was washed successively with water and brine. The organic solvent was removed in vacuum. The residue was purified by column chromatography on silica gel (CH2Cl2/PE/NH3?H2O, 8:3:0.1) to afford 22c (0.3354 g, 1.01 mmol, 90.2%).HRMS (ESI) (M+H)+ m/z 332.1389, Calcd for C20H18N3O2 332.1394. 1H NMR (CDCl3, 400 MHz), delta: 7.93 (s, 1 H, H-imidazolyl), 7.55 (d, J = 8.1 Hz, 2 H, H-phenyl), 7.45-7.29 (m, 9 H, H-imidazolyl, H-phenyl), 5.25-5.15(m, 3 H, -NH-, -CH2-O-), 4.28 (s, 2 H, -NH-CH2-).

The chemical industry reduces the impact on the environment during synthesis 1-(4-Bromophenyl)imidazole. I believe this compound will play a more active role in future production and life.

Reference:
Article; Li, Xue-Meng; Lv, Wei; Guo, Si-Yang; Li, Ya-Xin; Fan, Bing-Zhi; Cushman, Mark; Kong, Fan-Sheng; Zhang, Jun; Liang, Jian-Hua; European Journal of Medicinal Chemistry; vol. 171; (2019); p. 235 – 254;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 10040-96-7, name is 1-(4-Bromophenyl)imidazole, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 10040-96-7

Pd(PPh3)4 (112 mg, 96.7 mumol) was added to a mixture of 6 (600 mg, 0.967 mmol) and 1-(4-bromophenyl)-1H-imidazole (863 mg, 3.87 mmol) in aqueous Na2CO3 (2 M, 2.0 mL, 4.0 mmol) and anhydrous THF (18.0 mL), and the solution was stirred at room temperature for 15 min. The resulting two-phase system was refluxed under stirring overnight, and was then allowed to cool to room temperature. To this was added water (50 mL), and the mixture was extracted with CHCl3 (100 mL¡Á3). The organic layer was washed with water (50 mL), dried over anhydrous MgSO4, and filtered. After the solvent was removed by evaporation, the residue was subjected to SEC fractionation to obtain 2 (516 mg, 79%) as a bluish white solid. Mp: 251.8-252.0 C. IR (KBr, cm-1): 1523, 1305, 1273, 1139, 1114, 1055, 989. 1H NMR (500 MHz, CDCl3): delta 7.89 (s, 2H, ArH), 7.65 (d, J=8.6 Hz, 4H, PhH), 7.42 (d, J=8.6 Hz, 4H, PhH), 7.32 (s, 2H, ArH), 7.25 (s, 2H, ArH), 2.01 (s, 6H, CH3). 13C NMR (125 MHz, CDCl3): delta 142.1, 140.9, 136.9, 135.6, 132.7, 130.9, 127.1, 126.2, 123.1, 122.0, 118.2, 14.8. MS (ESI+): m/z=653 [M+H]+. Anal. Calcd for C33H22F6N4S2: C, 60.73; H, 3.40; N, 8.58. Found: C, 60.74; H, 3.48; N, 8.45.

According to the analysis of related databases, 10040-96-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Iida, Hiroki; Umebayashi, Naofumi; Yashima, Eiji; Tetrahedron; vol. 69; 52; (2013); p. 11064 – 11069;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 10040-96-7, 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. 10040-96-7, name is 1-(4-Bromophenyl)imidazole, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of 4 (1.01 g, 1.22 mmol), CuI (23 mg, 0.12 mmol),PdCl2(PPh3)2 (45 mg, 0.064 mmol) and triethylamine (0.26 mL,1.86 mmol) in acetonitrile (10 mL), 2-amino-5-bromopyrimidine(635 mg, 3.65 mmol) were added. The reaction mixture wasrecharged with Ar and stirred at 80 C for 4 h in a sealed tube.The mixture was extracted with ethyl acetate and the organic layerwas washed with water and brine successively. The organic solventwas removed in vacuo. The residue was purified by column chromatography on silica gel (CH2Cl2/C2H5OH/NH3H2O, 10:0.6:0.1) toafford 20-OAc-3f (156 mg, 0.17 mmol, 13.9%).A solution of 20-OAc-3f (156 mg, 0.17 mmol) in MeOH (20 mL)was stirred at 65 C for 3H. The organic solvent was removed invacuo. The residue was purified by preparative TLC (petroleumether/acetone/triethylamine, 5:5:0.2) to yield analytically pureproduct 3f (14 mg, 0.015 mmol, 9.4%).

The chemical industry reduces the impact on the environment during synthesis 1-(4-Bromophenyl)imidazole. I believe this compound will play a more active role in future production and life.

Reference:
Article; Han, Xu; Lv, Wei; Guo, Si-Yang; Cushman, Mark; Liang, Jian-Hua; Bioorganic and Medicinal Chemistry; vol. 23; 19; (2015); p. 6437 – 6453;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 10040-96-7, 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. 10040-96-7 name is 1-(4-Bromophenyl)imidazole, 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.

22.0g of 1- (4-bromophenyl) -1H-imidazole,27.8g of 10-iodocamphor and 50mL of N, N-dimethylformamide were sequentially added to a three-necked flask equipped with a stirrer, a thermometer and a condensing reflux device.The reaction is carried out at 130 C, and the reaction takes about 4 hours to complete the reaction of one of the raw materials.After cooling, 50 mL of ethyl acetate was added to precipitate the product, and the crude product of camphoryl imidazole iodide was filtered to obtain the target compound by recrystallization from ethanol. The product characterization data is as follows: 80% yield,

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(4-Bromophenyl)imidazole, and friends who are interested can also refer to it.

Reference:
Patent; Nanjing Forestry University; Wang Shifa; Bian Tiancen; Zhao Yuxun; Xu Xu; Yang Yiqin; Gu Wen; (13 pag.)CN110272344; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem