Tag: M.W=200-300

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 185122-74-1 as follows. Computed Properties of C9H10BrN

At 0 0C and under protective atmosphere, a solution of 2-Propanesulfonyl chloride (1 1.87 ml_, 121 mmol) in DCM (121 ml.) was added gradually to a solution of 5-bromo-2,3- dihydro-1 H-inden-1 -amine (12.8 g, 60.4 mmol) and 1 ,8-Diazabicyclo[5.4.0]undec-7-ene (4.83 ml_, 32.1 mmol) in Dichloromethane (300 ml_). The reaction was stirred at rt overnight. The reaction mixture was washed with 1 N KHSO4 (1x) and sat NaHCObeta (2x) before being dried on Na2SO4 and solvent evaporated in vacuo to afford a green oil. Purification by column chromatography (25% EtOAc in heptane) afforded the title compound as a white solid.(6.0 g, 31 %). MS (ESI) : m/z [M – H]” 317.0

According to the analysis of related databases, 185122-74-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; N.V. Organon; GILLEN, Kevin James; GILLESPIE, Jonathan; JAMIESON, Craig; MACLEAN, John Kinnaird Ferguson; MOIR, Elizabeth Margaret; RANKOVIC, Zoran; WO2010/115952; (2010); A1;,
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Related Products of 21524-34-5, 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 21524-34-5 as follows.

EXAMPLE TEN: Synthesis of Ligand 7; An oven-dried three-neck 250 mL round bottom flask, which was equipped with a magnetic stir bar and charged with magnesium shavings (559 mg, 24.3 mmol), was fitted with a reflux condenser, addition funnel, and glass stopper. The flask was purged with argon and then THF (15 mL) and 2,4,6-triisopropylbromobenzene (2.83 g, 10 mmol) were added via syringe. The reaction mixture was heated to reflux and 1 ,2-dibromethane (40 uL) was added via syringe. The reaction was allowed to stir at reflux for 1 h and then the addition funnel, which was charged with l,2-dibromo-3,4,5,6-tetramethylbenzene (2.92 g, 10 mmol) in 40 mL of THF, was opened and the solution was added over a 1 h period. The mixture was stirred for 5 h at reflux and then cooled to room temperature where CuCl (1.0 g, 10 mmol) was added quickly to the reaction mixture. Next, ClPCy2 (2.65 mL, 10 mmol) was then added in a dropwise fashion and the reaction mixture was heated to 75 0C for 60 h. The reaction mixture was then cooled to room temperature, diluted with EtOAc, washed 3 times with 30% NH4OH, dried over MgSO4, and concentrated under reduced pressure. The crude material was recrystallized from benzene to yield the product as a white solid (1.507 g, 28% yield). 1H NMR (300 MHz, CDCl3) delta: 7.36 (s, 5H), 7.15 (s, 2H), 2.99 (septet, J= 7.0 Hz, IH), 2.44 (s, 3H), 2.35-2.14 (m, HH), 1.98 (s, 2H), 1.80-1.44 (m, 14H), 1.39-1.04 (m, 22H), 0.91 (d, J= 6.5 Hz, 6H) ppm. 13C NMR (75 MHz, CDCl3) delta: 150.9, 145.8, 145.4, 144.6, 140.0, 138.5, 135.8, 135.6, 135.5, 135.5, 128.6, 124.3, 40.2, 39.9, 35.4, 35.2, 34.5, 30.7, 29.5, 27.8, 27.7, 27.4, 27.2, 25.9, 25.0, 24.6, 21.2, 20.8, 17.7, 17.3 ppm (Observed complexity is due to P-C splitting). 31P NMR (121 MHz, CDCl3) delta: 16.33 ppm.

According to the analysis of related databases, 21524-34-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MASSACHUSETTS INSTITUTE OF TECHNOLOGY; WO2009/76622; (2009); A2;,
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Synthetic Route of 626-40-4,Some common heterocyclic compound, 626-40-4, name is 3,5-Dibromoaniline, molecular formula is C6H5Br2N, 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 5.018 (0.02 muM) 3, 5 – dibromoaniline and 9.350 g (0.05 muM) (6 – aminonaphthalen – 2 – yl) boronic acid is added to a 500 ml three-neck bottle in, adding 400 ml tetrahydrofuran (THF), then adding 2 mol/L potassium carbonate solution of 75 ml, and add 0.5 ml of aliquat 336, magnetic stirring and open the argon gas, oil bath is heated to 75 C after, adding 0.020 g […] palladium, reflux reaction 24 h, the reaction liquid is poured into the water in the, a large amount of precipitate out. For funnel, evaporating the solvent under reduced pressure. The product in order to dichloromethane: hexane=3:1 ([…]) as the mobile phase silica gel as stationary phase makes the column chromatographic purification, collecting products and turns on lathe does, in 90 C drying in vacuum 24 h, to obtain the target product 5.632 g, yield is 75%.

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

Reference:
Patent; Hunan University of Technology; Ding Qian; Tan Jinghua; Liu Yiwu; Fu Hao; (20 pag.)CN109053466; (2018); A;,
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Reference of 73918-56-6,Some common heterocyclic compound, 73918-56-6, name is 2-(4-Bromophenyl)ethanamine, molecular formula is C8H10BrN, 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. BOC2O (818 mg, 3.75 mmol, 1.5 eq.) was added to a stirred solution of 2-(4- bromophenyl)ethanamine (500 mg, 2.5 mmol, 1.0 eq.) and TEA (1.5 ml, 7.5 mmol, 3.0 eq.) in DCM (25 ml) at 0 0C and resulting reaction mixture is stirred at 25 0C for 6 h. The reaction mixture was diluted with DCM (75 ml), washed with water (2 x 50 ml) and brine (50 ml) and dried over Na2SO4. The solvent was evaporated under reduced pressure and the residue triturated with hexanes to yield the desired product as an off white solid.Yield: 100 % (750 mg, 2.5 mmol)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(4-Bromophenyl)ethanamine, its application will become more common.

Reference:
Patent; GRUeNENTHAL GMBH; MERLA, Beatrix; OBERBOeRSCH, Stefan; REICH, Melanie; SCHUNK, Stefan; JOSTOCK, Ruth; HEES, Sabine; ENGELS, Michael; GERMANN, Tieno; BIJSTERVELD, Edward; WO2010/99938; (2010); A1;,
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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. 21524-34-5, name is 2-Bromo-1,3,5-triisopropylbenzene, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2-Bromo-1,3,5-triisopropylbenzene

General procedure: Ligand comparison reactions were setup at the same time using the same batches of reagents. In a N2 filled glove-box, a microwave vialwas charged with a magnetic stir bar, Pd2(dba)3 (2.3 mg, 0.0025mmol), the respective ligand L1-L5 (0.010 mmol), K3PO4 (424 mg, 2.00 mmol), and 2-biphenyboronic acid (9; 158 mg, 0.800 mmol). Degassed (argon sparge) toluene (1.3 mL) followed by bromide 8 (0.169 mL, 0.667 mmol) were added, and the vial was sealed with acrimp-cap septum and removed from the glove-box. The reaction vialwas then inserted into a heating block pre-heated to 80 C. Aliquots were removed using argon-purged syringes and quenched into MeOH and analyzed by UPLC. After complete consumption of the starting aryl bromide (2 h), the reaction mixture was cooled to r.t. and partitioned between H2O and CH2Cl2. The organic layer was collected,dried (anhyd Na2SO4), and concentrated in vacuo. The yield of thecrude mixture was determined by 1HNMR spectroscopy using dimethyl fumarate as the analytical standard.

According to the analysis of related databases, 21524-34-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhang, Yongda; Lao, Kendricks S.; Sieber, Joshua D.; Xu, Yibo; Wu, Linglin; Wang, Xiao-Jun; Desrosiers, Jean-Nicolas; Lee, Heewon; Haddad, Nizar; Han, Zhengxu S.; Yee, Nathan K.; Song, Jinhua J.; Howell, Amy R.; Senanayake, Chris H.; Synthesis; vol. 50; 22; (2018); p. 4429 – 4434;,
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Synthetic Route of 4263-52-9, A common heterocyclic compound, 4263-52-9, name is Sodium 2-bromoethanesulphonate, molecular formula is C2H4BrNaO3S, 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: A solution of 1mmol of chloride salt 1a or 2a in distilled water was treated with equimolar quantity of various salts (NaBF4, KPF6, 2-BrCH2CH2SO3Na). The reaction mixture was stirred at room temperature for 12h. Next, the reaction mixture was extracted twice with CH2Cl2. The organic layer was dried over anhydrous Na2SO4 and then CH2Cl2 was evaporated on a rotary evaporator to give various chiral ionic liquids 1b-d and 2b-d. 4.4.6 1-[(-)-Borneoxycarbonylmethylene]-3-methyl benzimidazolium 2-bromoethylsulfonate [ABoMBI]OSO2CH2CH2Br 2d Off-white solid Yield = 83%, mp = 96-98 C, [alpha]D25 = -15.6 (c 0.25, EtOH). 1H NMR (CDCl3, 400 MHz): delta 10. 35 (s, 1H), 7.78-7.68 (d, 1H, Ar), 7.60 (s, 3H, Ar), 5.47 (s, 2H NCH2), 5.44-5.35 (d, 1 H), 4.13 (s, 3H N-CH3), 3.60-3.52 (t, 2H), 3.20-3.07 (t, 2H), 2.31-2.19 (m, 1H), 1.72-1.56 (m, 3H), 1.19 (s, 3H), 1.02-0.97 (d, 1H), 0.80 (s, 6H), 0.74 (s, 3H). 13C NMR (CDCl3, 400 MHz): delta 166.09, 144.39, 131.67, 131.47, 127.46, 127.32, 113.07, 112.93, 83.16, 54.40, 48.93, 47.91, 44.64, 36.34, 33.76, 29.59, 27.79, 26.87, 26.29, 19.58, 18.72, 13.47. EI-MS: m/z = 327 [M+cation], m/z = 312 [M+cation-CH3].

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; Singh, Avtar; Chopra, Harish Kumar; Tetrahedron Asymmetry; vol. 27; 11-12; (2016); p. 448 – 453;,
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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. 58971-11-2, name is 3-Bromophenethylamine belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C8H10BrN

To a mixture of 2-(3-bromophenyl)ethanamine (485 mg, 2.42 mmol) and K2CO3 (469 mg, 3.39 mmol) in acetonitrile (7.3 mL) was added 1-bromo-2-methoxyethane (228 muL, 2.42 mmol), and the mixture was stirred ON at rt. The mixture was then heated at reflux for 6 h. An additional portion of 1-bromo-2-methoxyethane (75 muL, 0.80 mmol) was added, and heating was continued ON. The reaction mixture was filtered. The filtrate was concentrated, and residue purified by flash chromatography to provide 37A (189 mg, 30.2%). MS(ESI) m/z 257.9 (M+H).

The synthetic route of 58971-11-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SMALLHEER, Joanne M.; KICK, Ellen K.; VALENTE, Meriah Neissel; HU, Carol Hui; HALPERN, Oz Scott; JUSUF, Sutjano; (133 pag.)WO2018/5336; (2018); A1;,
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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. 615-59-8, name is 1,4-Dibromo-2-methylbenzene, A new synthetic method of this compound is introduced below., Product Details of 615-59-8

(1) 2,5-dibromotoluene (10 mmol, 2.5 g), 4-methoxycarbonylbenzeneboronic acid (24 mmol, 4.33 g) under N2 protection.caesium fluoride (40 mmol, 6.0 g) was placed in a 250 mL three-necked flask, and 5% (1.2 to 2.0 g) of Pd (PPh3) catalyst was added.100 mL of anhydrous THF was used as a solvent, and refluxed at 67 C.After completion of the reaction, the product was isolated by silica gel column chromatography (petroleum ether, dichloromethane) to give a pink solid 2.91 g, yield 81%.

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; Shandong Normal University; Dong Yubin; Wang Jiancheng; Liu Congxue; Hu Yuhong; (14 pag.)CN108640906; (2018); A;,
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. 54962-75-3, name is 3-Bromo-5-(trifluoromethyl)aniline, This compound has unique chemical properties. The synthetic route is as follows., Safety of 3-Bromo-5-(trifluoromethyl)aniline

3-bromo-5-trifluoromethylaniline (48 g, 0.2 mol) was added to a three-necked flask equipped with argon,4-methylimidazole (19.7 g, 0.24 mol), cuprous iodide (5.7 g, 0.03 mol)8-hydroxyquinoline (4.4 g, 0.03 mol)(30g, 0.22mol) and 300ml of DMSO, stirred and heated to 120 C for 24 h, followed by TLC. After the reaction was completed, the mixture was cooled to 50 C. 200 ml of 14% aqueous ammonia was added and stirring was continued for 1 h. Water and ethyl acetate were extracted three times. The organic phases were combined, washed with saturated brine, dried over anhydrous magnesium sulfate, filtered and the solvent was removed by rotary distillation.Then, the solvent was cooled in a refrigerator, and the precipitated crystals were filtered and dried to obtain 33.7 g of pale green needle-like crystals in a yield of 70%.

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 54962-75-3.

Reference:
Patent; Zhejiang Dade Pharmaceutical Group Co., Ltd.; Wang Jianping; Wang Jianguo; (14 pag.)CN107226809; (2017); A;,
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Electric Literature of 112734-22-2,Some common heterocyclic compound, 112734-22-2, name is (4-Bromo-2-fluorophenyl)methanamine, molecular formula is C7H7BrFN, 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 solution of ethyl 2-(4-cyano-2,6-difluorophenoxy)-4-formylnicotinate (0.30 g) obtained in Reference Example 229 and (4-bromo-2-fluorophenyl)methanamine (0.20 g) in THF (6 mL) was stirred at room temperature for 4 hr. The reaction mixture was concentrated, to a solution of the residue in acetic acid (6 mL) was added sodium triacetoxyhydroborate (0.29 g) at room temperature, and the mixture was stirred under an argon atmosphere at room temperature for 2 hr. The reaction mixture was neutralized with saturated aqueous sodium hydrogen carbonate solution, and the mixture was diluted with ethyl acetate. The organic layer was separated, washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. To a solution of the obtained 4-((2-(4-bromo-2-fluorobenzyl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-4-yl)oxy)-3,5-difluorobenzonitrile (0.20 g), ((1-methyl-1H-pyrazol-4-yl)boronic acid (0.058 g) and 2M aqueous sodium carbonate solution (0.63 mL) in DME (4 mL) was added [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.031 g), and the mixture was stirred under an argon atmosphere at 80C overnight. The reaction mixture was diluted with water and ethyl acetate. The organic layer was separated, washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel chromatography (hexane-ethyl acetate), and solidified with ethyl acetate to give the title compound (0.017 g). MS: [M+H]+ 476.1 1H NMR (300 MHz, CDCl3) delta 3.96 (3H, s), 4.45 (2H, s), 4.86 (2H, s), 7.16-7.20 (1H, m), 7.22 (1H, d, J = 4.2 Hz), 7.26 (1H, brs), 7.36 (2H, d, J = 6.6 Hz), 7.40-7.47 (1H, m), 7.62 (1H, s), 7.74 (1H, s), 8.16 (1H, d, J = 5.1Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (4-Bromo-2-fluorophenyl)methanamine, its application will become more common.

Reference:
Patent; Takeda Pharmaceutical Company Limited; SUGIMOTO, Takahiro; NAKAMURA, Minoru; SAKAMOTO, Hiroki; SUZUKI, Shinkichi; YAMADA, Masami; KAMATA, Makoto; KOJIMA, Takuto; FUJIMORI, Ikuo; SHIMOKAWA, Kenichiro; EP2921480; (2015); A1;,
Bromide – Wikipedia,
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