Month: May 2021

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. 376646-62-7, name is (4-Bromo-2-methylphenyl)methanamine, A new synthetic method of this compound is introduced below., Recommanded Product: (4-Bromo-2-methylphenyl)methanamine

To a solution of tert-butyl 3-isopropoxyazetidine-1-carboxylate (345 mg, 1.6 mmol) in MeOH (30 mL) was dropwise added SOCl2 (1.88 g, 16 mmol, 10 eq). The mixture was stirred at 65 °C for 1 h and the solvent was evaporated to afford a residue which was dissolved in DCM (6 mL) and treated with triphosgene (189 mg, 0.64 mmol) and TEA (800 mg, 8.0 mmol). After the mixture was stirred at rt for 0.5 h 4-bromo-2-methylbenzyl amine (312 mg, 1.57 mmol, 1 eq) was added and the mixture was stirred for another 3 h. The solvent was concentrated in vacuo to afford a residue which was purified by prep-HPLC (CH3CN/H2O with 0.05percent TFA as mobile phase) to give the title compound (150 mg, 27percent) as a yellow solid. ESI-MS (M+H)+: 341.0.

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; BIOGEN IDEC MA INC.; SUNESIS PHARMACEUTICALS, INC.; HOPKINS, Brian T.; MA, Bin; CHAN, Timothy Raymond; KUMARAVEL, Gnanasambandam; MIAO, Hua; BERTOLOTTI-CIARLET, Andrea; OTIPOBY, Kevin; WO2015/89327; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 117635-21-9, These common heterocyclic compound, 117635-21-9, name is 1,4-Dibromo-2,5-dihexylbenzene, 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 toluene (400 mL) solution of benzophenoeimine (18.1 g, 100 mmol), 1,4-dibromo-hexyl benzene (20 g, 50 mmol), t-BuONa (10 g), and (DPPF)2PdCl2 (2 g) was refluxed under argon. The mixture was refluxed for 72 hours and then cooled to room temperature. Water (70 mL) and aqeous HC1 (37%, 70 mL) were added to the mixture, which was then refluxed for 10 hours and cooled to room temperature. The solvent was removed by rotary evaporator. The solid was stirred with ethyl ether (300 mL) for 2 days, then filtered, washed with a small amount of ether, and dried, which was stirred in ether (200 mL) with aqueous NaOH (5 M, 300 mL), The ether phase was separated and dried over MgSO4 and run through a short, silica gel column (6 cm×6 cm). The solvent was removed to leave a dark brown solid, which was dissolved in eihanol (50 mL). After sitting overnight, 2,5-dihyxylbenzene-1,4-diamine needles had formed in the solution. The needles were collected through filtration (yield: 6 g, 43%). [0065] FIG. 1a depicts a 1H NMR spectrum of 2,5-dihyxylbenzene-1,4-diamine in CDCl3. [0066] FIG. 1b depicts a ChemDraw-simulated 1H NMR spectrum of 2,5-dihyxylbenzene-1,4-diamine. [0067] FIG. 2a depicts a 13C NMR spectrum of 2,5-dihyxylbenzene-1,4-diamine in CDCl3. [0068] FIG. 2b depicts a ChemDraw-simulated 13C NMR spectrum of 2,5-dihyxylbenzene-1,4-diamine.

Statistics shows that 1,4-Dibromo-2,5-dihexylbenzene is playing an increasingly important role. we look forward to future research findings about 117635-21-9.

Reference:
Patent; PHILLIPS 66 COMPANY; Huang, Hui; US2014/58110; (2014); 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. 1435-54-7, name is 1,3-Dibromo-2-fluorobenzene, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 1,3-Dibromo-2-fluorobenzene

Scheme 4-1: In Step 1 the appropriately substituted dibromo species is coupled with an appropriate boronic acid as known in the art to form a mixture of biaryl and triaryl products from which the desired biaryl compound is isolated. In Step 2 the appropriately substituted biaryl species is converted to the Grignard reagent with activated magnesium. In Step 3 the appropriately substituted aldehyde is treated with the previously prepared Grignard reagent to form an alcohol. In Step 4 the appropriately substituted alcohol is converted to a bromide as known in the art with carbon tetrabromide and triphenyl phosphine. In Step 5 the appropriately substituted bromide is converted to the Grignard reagent with activated magnesium.

According to the analysis of related databases, 1435-54-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ACHILLION PHARMACEUTICAL, INC.; WILES, Jason Allan; PHADKE, Avinash S.; DESHPANDE, Milind; AGARWAL, Atul; CHEN, Dawei; GADHACHANDA, Venkat Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; BARRISH, Joel Charles; GREENLEE, William; EASTMAN, Kyle J.; (0 pag.)WO2018/160891; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 959992-62-2, 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. 959992-62-2, name is 6-Bromo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine, This compound has unique chemical properties. The synthetic route is as follows.

In a 10 ml microwave reactor vial were placed (R)-4-((R)-1-((1-cyclopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazol-7-yl)oxy)ethyl)pyrrolidin-2-one (150.0 mg, 0.36 mmol), 6-bromo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine (172.5 mg, 0.8 mmol), and Pd(PPh3)4 (21.1 mg, 0.02 mmol) in DME (1 ml) and 2N Na2CO3 (1 ml). The mixture was sonicated and degassed for 1 min, placed in the microwave reactor, and heated at 135 C. for 15 min. Then it was directly loaded onto the pre-packed silica cartridge and purified using flash chromatography (100% dichloromethane to 25% MeOH in dichloromethane). The fractions were collected, concentrated, and further purified by reverse phase flash chromatography. The fractions were collected, neutralized with sat. NaHCO3, and extracted with EtOAc. The combined organic layers were washed with water and brine, dried (Na2SO4), filtered, and concentrated to give 52.7 mg (34%) of (R)-4-((R)-1-((1-cyclopropyl-5-(3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-1H-benzo[d]imidazol-7-yl)oxy)ethyl)pyrrolidin-2-one.

The chemical industry reduces the impact on the environment during synthesis 6-Bromo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Gilead Scientific Systems, Inc.; Cory, Kevin S; Doo, Jimin; Farrand, Julie; Guerrero, Juan A; Katana, Ashley A; Cato, Daryl; Laisaweed, Scott I; Lee, Jiayao; Lingco, John O; Nicolaus, May; Notte, Gregory; Phyen, Hyeoung-Jung; Sangy, Michael; Sumit, Arun C; Adam J, Surayyah; Stephens, Cork L; Venkatraman, Chandrasekar; Watkins, William J; Yang, Jong Yu; Jabloki, Jeff; Jifel, Shiela; Ro, Jennifer; Lee, Sung H; Jao, Chung Dong; Grove, Jeffery; Su, Jianjun; Blomgren, Peter; Mitchell, Scott A; Shyung, Jin Ming; Chandrasekar, Jayaraman; (460 pag.)KR2016/37198; (2016); A;,
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. 18869-30-2, name is (E)-1,2-Bis(4-bromophenyl)ethene, A new synthetic method of this compound is introduced below., Product Details of 18869-30-2

Step 3: Synthesis of (E)-4,4′-bis[4-(10-phenyl-9-anthryl)phenyl]stilbene; 2.0 g (5.9 mmol) of (E)-4,4′-dibromostilbene, 4.9 g (13 mmol) of 4-(10-phenyl-9-anthryl)phenylboronic acid, 0.053 g (0.24 mmol) of palladium (II) acetate, and 0.25 g (0.83 mmol) of tri(ortho-tolyl)phosphine were put into a 100 mL three-necked flask. Then, the atmosphere in the flask was substituted with nitrogen. 30 mL of ethylene glycol dimethyl ether (abbreviation: DME) and 18 mL (35 mmol) of an aqueous potassium carbonate solution (2.0 mol/L) were added to the mixture and the mixture was refluxed at 90 C. for 6 hours to be reacted. After the reaction was completed, a precipitate in the reaction mixture was collected by suction filtration. The collected precipitate was washed with toluene; then 4.7 g of objective (E)-4,4′-bis[4-(10-phenyl-9-anthryl)phenyl]stilbene (abbreviation: PAP2S) was obtained as a light yellow powdered solid in a yield of 94%. A synthetic scheme of (E)-4,4′-bis[4-(10-phenyl-9-anthryl)phenyl]stilbene is illustrated below (synthetic scheme c-1). A 1H NMR data of the obtained (E)-4,4′-bis[4-(10-phenyl-9-anthryl)phenyl]stilbene is described below. 1H NMR (CDCl3, 300 MHz): delta=7.14-7.21 (m, 2H), 7.30-7.44 (m, 11H), 7.48-7.52 (m, 5H), 7.54-7.61 (m, 8H), 7.63-7.73 (m, 8H), 7.77-7.81 (m, 6H), 7.83-7.91 (m, 4H).The 1H NMR chart is illustrated in each of FIGS. 8A and 8B. It is to be noted that the range of 7.0 to 8.0 ppm in FIG. 8A is expanded and illustrated in FIG. 8B.

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; Semiconductor Energy Laboratory Co., Ltd.; US2008/81934; (2008); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 7314-86-5,Some common heterocyclic compound, 7314-86-5, name is 1,3,5,7-Tetrabromoadamantane, molecular formula is C10H12Br4, 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.

Compound (1) of Example Ia was reacted with sodium cyanide in DMSO under irradiation at 254 nm as described in G. S. Lee et al., Org. Lett. Vol. 6, No. 11, 2004, 1705-1707, scheme 2a, (c). Tetracyanoadamantane was obtained in 63% yield.

The synthetic route of 7314-86-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GE HEALTHCARE AS; WO2009/21948; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 90562-10-0, A common heterocyclic compound, 90562-10-0, name is 1-Bromo-4-(3-bromopropyl)benzene, molecular formula is C9H10Br2, 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.

The starting material was prepared using an analogous procedure to that described in Example 35 for the preparation of 3-(4-allyloxyphenyl)-1-methoxypropane but starting from 3-(4-bromophenyl)propyl bromide. There was thus obtained 3-(4-bromophenyl)-1-(methoxy)propane; NMR (CDCl3): 1.8-2.0(2H, m), 2.6-2.7(2H, t), 3.3-3.4(5H, m), 7.0-7.1(2H, d) and 7.3-7.4(2H, d).

The synthetic route of 90562-10-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zeneca Limited; US5919793; (1999); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 1123172-38-2, 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. 1123172-38-2 name is 1-Bromo-3-(tert-butyl)-5-fluorobenzene, 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.

238 mg of bromo-3-tert-butyl-5-fluorobenzene (1.03 mmol; 1.03 eq.), 319 mg of methyl 1-[3-(4,4,5,5- tetramethyl- 1 ,3,2-dioxaborolan-2-yl)phenyl]azetidine-3-carboxylate (preparation 10; 1.00 mmol; 1 eq) and 4 mE of dioxane were added to a 12 mE Q-Tube reaction vessel. The medium was purged under vacuum and under argon. 41 mg of Pd(dppf)C12CH2C12 (0.05 mmol; 0.05 eq) and 415 mg of ground K2C03 (3.00 mmol; 3.00 eq.) were added, and then the reactor was sealed and heated at 114 C. for 20 h. The reaction medium was then filtered, rinsed with DCM and concentrated under reduced presure. The residue was purified by flash chromatography on silica using a cyclohexane/ 0% to 5% (cyclohexane/ethyl acetate) gradient. 237 mg of the title compound were obtained in the form of a yellow syrup.11071] Yld: 69%. ?H NMR (300 MHz, CHC13-d) oeppm 1.34 (s, 9H)3.53-3.66 (m, 1H) 3.75 (s, 3H) 4.05-4.11 (m, 4H) 6.48 (dd,J=8.0, 2.3 Hz, 1H) 6.6 (t, J=2.0 Hz, 1H) 6.94-6.99 (m, 1H)7.04 (m, 1H) 7.07 (m, 1H) 7.29 (t, J=7.8 Hz, 1H) 7.33 (t,J=1.7 Hz, 1H). LC-MS: mlz (M+H): 342.

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

Reference:
Patent; INVENTIVA; BOUBIA, Benaissa; MASSARDIER, Christine; GUILLIER, Fabrice; POUPARDIN, Olivia; TALLANDIER, Mireille; AMAUDRUT, Jerome; BONDOUX, Michel; FEENSTRA, Roelof Williem; VAN DONGEN, Maria Johana Petronella; (207 pag.)US2017/66717; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 106-37-6, 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. 106-37-6 name is 1,4-Dibromobenzene, 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.

At 80C, 4-dibenzofuranboronic acid (13.3g), 1,4-dibromobenzene (10g), tetrakis(triphenylphosphine)palladium (3.02g), toluene (158mL), ethanol (65mL), water (65mL), and potassium carbonate (21.69g) were stirred for 5 hours. The reaction was monitored by thin layer chromatography. Upon completion of the reaction, it was quenched with water (100mL) and extracted with ethyl acetate (100mL). The organic layer was extracted with water (3x30mL) and dried over anhydrous sodium sulfate. The ethyl acetate layer was collected through Celite and further purified by column chromatography. Following this, the ethyl acetate layer was evaporated to dryness under vacuum rotavap to yield 13.7g 4-(4′-bromophenyl)dibenzofuran.

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

Reference:
Patent; e-Ray Optoelectronics Technology Co., Ltd.; Ban, Ruman; Huang, Helong; Yao, Zhengcong; Xie, Bowei; Chen, Huixu; (34 pag.)CN105585555; (2016); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 51776-71-7, name is 1-Bromo-4-(difluoromethyl)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 51776-71-7, category: bromides-buliding-blocks

Example 38:; phit’i-Difluoroinethyl-phenoxyJ^^-dimethyl^.S-dihydro-benzofuran-beta-carboxylic acid (1 -methyl-1 H-pyrazol-3-yl)-amide; A mixture of 4-hydroxy-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid (1 -methyl-1 /-/-pyrazol-3-yl)- amide (31a) (102 mg, 0.36 mmol), 1-bromo-4-difluoromethyl benzene (110 mg, 0.53 mmol), Cs2CO3 (174 mg, 0.53 mmol) and CuI (1 mg) in DMF (5 mL) was heated for 2 hr at 16O0C in the microwave. The mixture was filtered and the filtrate was purified by reverse phase chromatograph to give a white solid (18 mg, 12% yield). 1H NMR (400 MHz, CDCI3) delta 9.92 (d, J=2.02 Hz, 1 H) 8.52 (s, 1 H) 7.72 (dd, .7=10.36, 1.77 Hz, 1 H) 7.64 (d, J=8.34 Hz, 1 H) 7.28 (s, 1 H) 7.09 (t, J=7.96 Hz, 1 H) 7.05 (s, 1 H) 6.97 (s, 1 H) 6.77 (d, J=2.02 Hz, 1 H) 3.78 (s, 3 H) 2.98 (s, 2 H) 1.51 (s, 6 H); LCMS for C22H21F2N3O3 m/z 414.00 (MH-H)+

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

Reference:
Patent; PFIZER PRODUCTS INC.; WO2007/122482; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary