Month: July 2021

These common heterocyclic compound, 699-03-6, name is 1-(4-Bromophenyl)-N-methylmethanamine, 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. Application In Synthesis of 1-(4-Bromophenyl)-N-methylmethanamine

General procedure: Aldehyde (3 mmol) was taken up in dry DCM (10 mL) in an oven dried round bottomed flask under an atmosphere of nitrogen. Acetic acid (1 mmol) was added and the reaction stirred at room temperature for 5 minutes. Amine (1 mmol) was then added and the reaction stirred at room temperature for 1 hour. The reaction was cooled to 0 C using an ice bath, then sodium triacetoxyborohydride (3 mmol) was added and the reaction warmed to room temperature and stirred until TLC indicated complete consumption of the amine. The reaction was quenched with saturated aqueous sodium bicarbonate solution. The organic layer was washed with three portions of saturated sodium bicarbonate, then acidified with concentrated hydrochloric acid. The organic layer was then washed with three portions of 2 M aqueous hydrochloric acid. The pH of the acidic washes was then adjusted to pH 10 using 4 M aqueous sodium hydroxide and the aqueous extracted with three portions of diethyl ether. The combined ether washes were dried with magnesium sulfate, filtered and concentrated to give crude product. The residue was then purified by flash column chromatography and sent to NKI for biological testing.

The synthetic route of 1-(4-Bromophenyl)-N-methylmethanamine has been constantly updated, and we look forward to future research findings.

Reference:
Article; Milne, Kirsty; Sun, Jianhui; Zaal, Esther A.; Mowat, Jenna; Celie, Patrick H.N.; Fish, Alexander; Berkers, Celia R.; Forlani, Giuseppe; Loayza-Puch, Fabricio; Jamieson, Craig; Agami, Reuven; Bioorganic and Medicinal Chemistry Letters; vol. 29; 18; (2019); p. 2626 – 2631;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 74586-53-1, A common heterocyclic compound, 74586-53-1, name is 3-Bromo-5-methylaniline, molecular formula is C7H8BrN, 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.

General procedure: 3-(trifluoromethyl) benzoic acid (511mg, 2.69mmol) was stirred in a solvent of 58 dimethyl formamide (10mL).The reaction solution was added with 59 HATU (1.12g, 2.96mmol), 72 DIPEA (890mul, 5.37mmol) and the appropriate substituted aromatic amine (500mg, 2.69mmol), followed by stirring for about 8h at room temperature. The reaction mixture was diluted with ethyl acetate and washed with a saturated aqueous sodium bicarbonate solution and saline. The organic layer thus obtained was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The resulting mixture was concentrated to give the crude product, which was purified by silica gel column chromatography (eluting with 0-5% EtOAc in 82 petroleum ether) to afford the 110 product as a white solid (815mg, 84%).

The synthetic route of 74586-53-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Qi; Dai, Yang; Ji, Yinchun; Shi, Huanyu; Guo, Zuhao; Chen, Danqi; Chen, Yuelei; Peng, Xia; Gao, Yinglei; Wang, Xin; Chen, Lin; Jiang, Yuchen; Geng, Meiyu; Shen, Jingkang; Ai, Jing; Xiong, Bing; European Journal of Medicinal Chemistry; vol. 163; (2019); p. 671 – 689;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 34699-28-0,Some common heterocyclic compound, 34699-28-0, name is 1-(4-Bromophenyl)-1,2,2-triphenylethylene, molecular formula is C26H19Br, 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.

Into a 250 mL two-necked round-bottom flask under nitrogen was slowly added n-butyllithium (1.6 M in hexane, 7.5 mL, 12 mmol) and a THF solution (80 mL) of 1-(4-bromophenyl)-1,2,2-triphenylethene (3) (4.11 g, 10 mmol) at -78C. After stirring for 3 h, 2.4 mL of trimethylborate (20 mmol) was added into the reaction mixture. The mixture was warmed to room temperature and the reaction was terminated by adding hydrochloric acid (2 M, 10 mL) after 12 h. The mixture was then poured into water and extracted with dichloromethane. The organic layer was washed with water and dried over magnesium sulfate. After filtration and solvent evaporation, the residue was purified by silica-gel column chromatography using n-hexane/ethyl acetate as eluent. White solid of 4-(1,2,2-Triphenylvinyl)phenylboronic acid (4) was obtained in 70% yield (2.6 g). 1H NMR (300 MHz, CDCl3), delta (TMS, ppm): 7.88 (d, 2H, J=8.1 Hz), 7.13-7.00 (m, 17H), 4.49 (s, 1H). 13C NMR (75 MHz, CDCl3), delta (TMS, ppm): 148.9, 144.2, 144.1, 144.09, 142.4, 141.4, 135.6, 133.5, 132.0, 131.6, 128.4, 128.3, 127.4, 127.2. HRMS (TOF): m/e 376.2030 (M+, calcd 376.1635).

The synthetic route of 34699-28-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY; TANG, Benzhong; HONG, Yuning; LEUNG, Wai Tung; US2013/59392; (2013); 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. 1435-51-4, name is 1,3-Dibromo-5-fluorobenzene, A new synthetic method of this compound is introduced below., Safety of 1,3-Dibromo-5-fluorobenzene

Cesium carbonate (11.4 g; 8.79 mmol) was added to a solution of 2-chloro-5-methylphenol (18; 2.5 g; 17.53 mmol) and NMP (16 mL). The resulting slurry was degassed and the flask alternately purged and refilled with nitrogen. 1,3-Dibromo-fluorobenzene (3.54 g; 28.13 mmol), TMHD (0.92 mL; 0.81 g; 4.41 mmol) and Cu(I)Cl (0.87 g; 8.79 mmol) were added sequentially and the reaction mixture was heated to 110 C. for 6 h. The reaction mixture was cooled to ambient temperature, filtered through a bed of CELITE and the filter cake washed thoroughly with EtOAc. The filtrate was washed sequentially with dilute HCl dilute NaOH, water and brine. The organic extract was dried (Na2SO4), filtered and evaporated. The residue was chromatographed on silica gel and eluted with hexane:Et2O which yielded 1.8 g (32%) of 37c as a colorless oil.

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; Roche Palo Alto LLC; US2004/198736; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 112734-22-2, 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. 112734-22-2 name is (4-Bromo-2-fluorophenyl)methanamine, 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.

Example 12 Preparation of (3R)-2′-(4-bromo-2-fluorobenzyl)spiro[pyrrolidin-3,4′(1’H)-pyrrolo[1,2-a]pyrazin]-1′,2,3′,5(2’H)-tetraone 2,5-Dimethoxytetrahydrofuran (7.4 g) and 2.5% aqueous acetic acid (50 g) were added to ethyl (2R)-2-amino-2-ethoxycarbonylsuccinimide (10 g)and the mixture was stirred at 70C for 1.5 hours. The reaction solution was cooled and insoluble materials were dissolved by addition of ethyl acetate (50 ml) and stirring. The mixture was placed for a while and the organic layer was separated from the aqueous layer, washed with brine, dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo, diisopropylether (37 g) and ethyl acetate (9.2 g) were added to the residue and diisopropylamine (6.2 g) was added and the mixture was stirred at 0-5C of inner temperature. The precipitated crystals were filtered, washed with diisopropylether and dried to give (2R)-2-ethoxycarbonyl-2-(pyrrol-1-yl)succinimide diisopropylamine salt(yield 88%). To a suspension of (2R)-2-ethoxycarbonyl-2-(pyrrol-1-yl)succinimide diisopropylamine salt (20.0 g) in ethyl acetate (100 ml), was added 20% aqueous sulfuric acid (16 ml) and the salt was dissolved. The solution was placed after stirring and the organic layer was separated with the aqueous layer. The organic layer was separated with the aqueous layer again after brine was added to the organic solution, and the mixture was stirred and placed. The organic layer was concentrated in vacuo, ethyl acetate (50 ml) and trichloroacetyl chloride (32.3 g) were added to the residue and the mixture was stirred under reflux for 6 hours. The reaction solution was cooled, ethyl acetate (134 ml) was added thereto and it was washed with brine, aqueous solution of sodium bicarbonate, 5% aqueous sulfuric acid and brine successively. The organic layer was concentrated in vacuo, N-methyl pyrrolidone (26 ml) and ethyl acetate(6.7 ml) were added and the residue was dissolved. The solution was cooled and diisopropylamine (9 g) was added thereto and the mixture was stirred. 4-Bromo-2-fluorobenzylamine (24.2 g) was added dropwise under ice-cooling and the mixture was stirred at 0-5C for 18 hours. Ethyl acetate (266 ml) was added to the reaction solution and it was washed with 5% aqueous sulfuric acid, aqueous solution of sodium bicarbonate, 5% aqueous sulfuric acid and brine successively. The organic layer was concentrated in vacuo, ethanol (100 ml) was added to the residue and it was dissolved under heating to reflux. Ethanol (33 ml) was evaporated, the concentrated solution was cooled with ice-water and the precipitated crystals were filtered and washed with ethanol. The resulting wet crystals were recrystallized from isopropanol (124 ml and 180 ml) twice to give (3R)-2′-(4-bromo-2-fluorobenzyl)spiro[pyrrolidin-3,4′(1’H)-pyrrolo[1,2-a]pyrazin]-1′,2,3′,5(2’H)-tetraone (yield 58%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (4-Bromo-2-fluorophenyl)methanamine, and friends who are interested can also refer to it.

Reference:
Patent; Dainippon Sumitomo Pharma Co., Ltd.; Katayama Seiyakusyo Co. Ltd.; EP2058300; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 57190-17-7,Some common heterocyclic compound, 57190-17-7, name is 2-Bromo-1,3-diisopropylbenzene, molecular formula is C12H17Br, 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: To a mixture of Pd(OAc)2 (23 mg, 0.1 mmol), DPE-Phos (125 mg,0.2 mmol), and Cs2CO3 (652 mg, 2.0 mmol) was added a solutionof 4a (496 mg, 1.0 mmol) and 2-bromo-1,3,5-trimethylbenzene(300 mg, 1.5 mmol) in 1,4-dioxane (15 mL) under N2, and the reactionmixture was heated at 110 C for 17 h with stirring. After coolingto r.t., and removal of solvents, the mixture was extracted withCH2Cl2 (3 × 20 mL), and the combined organic extracts werewashed with brine (20 mL) and dried (Na2SO4). Purification of theresidual oil by column chromatography on silica gel (hexanes-EtOAc, 10:1) afforded 5a

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-diisopropylbenzene, its application will become more common.

Reference:
Article; Zhu, Shifa; Wang, Chao; Zhao, Songxian; Xiao, Yelin; Hu, Lang; Huang, Zhipeng; Synthesis; vol. 46; 2; (2014); p. 212 – 224;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 452-74-4, A common heterocyclic compound, 452-74-4, name is 1-Bromo-2-fluoro-4-methylbenzene, molecular formula is C7H6BrF, 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.

3-Fluoro-4-bromotoluene (5.0 g, 27 mmol) in carbon tetrachioride (50 mE) was treated with N-bromosuccinimide (7.0 g, 40 mmol, 1.5 eq) and heated to 80 C. Henzoyl peroxide (65 mg, 0.27 mmol, 0.01 eq.) was added and heating was continued for 1 h. The reaction was then cooled to ambient temperature and filtered, and the filtercake was washed sparingly with chloroform. The filtrate was washed with water and brine, dried over Na2SO4, and concentrated to give crude 3-fluoro-4-bromobenzyl bromide as a clear oil which was used without thrther purification.

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; INFINITY PHARMACEUTICALS, INC.; BEHNKE, Mark L.; CASTRO, Alfredo C.; EVANS, Catherine A.; GRENIER, Louis; GROGAN, Michael J.; LIU, Tao; SNYDER, Daniel A.; TIBBITTS, Thomas T.; US2015/368278; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 153505-37-4, name is 4-Bromo-5-fluorobenzene-1,2-diamine belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C6H6BrFN2

4-bromo-5-fluorobenzene-1,2-diamine (5.00 g, 24.4 mmol) was solubilised in 1 ,4-dioxane (200 ml). 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi-1,3,2-dioxaborolane (7.43 g, 29.3 mmol), potassium acetate (12.0 g, 122 mmol) and dichlorobis(tricyclohexylphosphine)palladium(ll) (900 mg, 1 .22 mmol) were added and the mixture was stirred overnight at 1 10C. The mixture was filtered and the filtrate was concentrated under reduced pressure. The crude mixture was purified by flash chromatography on silica gel to give 3.23 g (90 % purity, 47 % yield) of the title compound. LC-MS (Method 2): Rt = 0.75 min; MS (ESIpos): m/z = 253 [M+H]+ 1H-NMR (400 MHz, DMSO-d6) _ [ppm]: 1.066 (0.59), 1 .156 (2.87), 1 .230 (16.00), 5.191 (1.07), 6.172 (1.00), 6.200 (1.04), 6.739 (0.89), 6.755 (0.89).

The synthetic route of 153505-37-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; LEFRANC, Julien; MENGEL, Anne; SCHULZE, Volker; CHRIST, Clara; PRINZ, Florian; WENGNER, Antje, Margret; STOeCKIGT, Detlef; BOeMER, Ulf; BADER, Benjamin; (288 pag.)WO2017/207534; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 108-85-0, The chemical industry reduces the impact on the environment during synthesis 108-85-0, name is Bromocyclohexane, I believe this compound will play a more active role in future production and life.

General procedure: Benzo[b]thiophene-3-carbaldehyde (40 mg, 0.25 mmol, 1.0 equiv),Pd(TFA) 2 (4.2 mg, 5 mol%), (4-FC 6 H 4 ) 3 P (9.5 mg, 12 mol%), DPEphos (8mg, 6 mol%), and Cs 2 CO 3 (122 mg, 0.375 mmol) were placed in atransparent Schlenk tube equipped with a stirring bar. The tube wasevacuated and filled with argon for three times. Degassed DMF (2.5mL) and tert-butyl bromide (51 mg, 0.375 mmol, 1.5 equiv) were add-ed via a gastight syringe. The reaction mixture was stirred under theirradiation of 36 W blue LEDs (distance app. 2.0-3.0 cm from thebulb) at r.t. for 24 h. The mixture was quenched with brine and ex-tracted with EtOAc (3 × 10 mL). The organic layers were combinedand concentrated under reduced pressure. The product was purifiedby flash column chromatography on silica gel using PE or a mixture of PEand EtOAc (10:1 v/v) as eluent; yield: 50.1 mg (92%); pale yellow liquid.

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, Bromocyclohexane, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Wang, Guang-Zu; Shang, Rui; Fu, Yao; Synthesis; vol. 50; 15; (2018); p. 2908 – 2914;,
Bromide – Wikipedia,
bromide – Wiktionary

22385-77-9, name is 1-Bromo-3,5-di-tert-butylbenzene, 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. COA of Formula: C14H21Br

Bromo-3,5-di-tert-butylbenzene (1.3 g, 5 mmole) was dissolved in THF (20 mL), to this solution was slowly added n-BuLi (1.6 M, 3.3 mL) at -78° C., the reaction was stirred at this temperature for 30 min, trimethyl borate (0.75 g, 7.5 mmole) was added all at once, stir over night while the reaction was allowed to slowly warm up to room temperature. Hydrochloric acid (6N, 5 mL) was added and stirred for 3 hrs at room temperature. Water (200 mL) was added, and the precipitate was collected, washed with water (10 mL.x.3), dried under vacuum to give titled compound.

The synthetic route of 22385-77-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Adams, Alan D.; Santini, Conrad; US2009/30012; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary