Category: bromides-buliding-blocks

Application of 771583-12-1, A common heterocyclic compound, 771583-12-1, name is 2-(Aminomethyl)-4-bromoaniline, molecular formula is C7H9BrN2, 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.

Step 2: 6-bromo-3.4-dihvdroquinazolin-2(1 H)-one; To a solution of triphosgene (0.445 g, 1.5 mmol) in tetrahydrofuran (20 mL) was added triethylamine (0.454 g, 4.5 mmol) dropwise at 0 0C under nitrogen. After stirring for 30 min, a solution of 2-(aminomethyl)-4-bromoaniline (0.201 g, 1 mmol) in tetrahydrofuran (10 mL) was added dropwise. The mixture was allowed to stir for 16 h at room temperature. The mixture was diluted with water (15 mL) and the pH of the resultant mixture was adjusted to 8 – 9 by the addition of 1 M aqueous sodium hydroxide. The mixture was extracted three times with ethyl acetate (30 mL). The combined organic layer was dried over sodium sulfate and concentrated. The residue was purified by re- crystallization from a mixture o dichloromethane and diethyl ether to give the title compound (0.13 g, 57.5%) as a yellow solid. 1 H NMR (400MHz, DMSO-Cf6) delta ppm 9.12 (s, 1 H), 7.29 (S, 1 H), 7.27(d, J = 8.4 Hz, 1 H), 6.87 (s, 1 H), 6.70 (d, J = 8.4 Hz, 1 H), 4.28 (s, 2H).

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; PFIZER INC.; ARHANCET, Graciela Barbieri; CASIMIRO-GARCIA, Agustin; CHEN, Xiangyang; HEPWORTH, David; MEYERS, Marvin Jay; PIOTROWSKI, David Walter; RAHEJA, Raj Kumar; WO2010/116282; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

10016-52-1, name is 2,8-Dibromodibenzo[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. HPLC of Formula: C12H6Br2O

2,8-Dicyanodibenzofuran 11. A mixture of 2,8-dibromodibenzofuran (10, 10.93 g, 33.53 mmol) and copper(I) cyanide (8.91 g, 102 mmol) in DMF (80 mL) was refluxed under N2 for 9 h. The reaction mixture was poured into ice-water (300 mL). The precipitated solid was filtered off and stirred overnight in a solution of ethylenediamine (50 mL) in water (300 mL). The solid was filtered off, washed with water, then stirred in 10% sodium cyanide solution (100 mL) overnight. The solid was further purified by suspension in hot ethanol (100 mL) to give a white powder (6.97 g, 95.2%): mp 298-300 C. (dec.) (Lit. [37] 299 C.); HPLC method 1 tR=24.07 min (97.3 area %); 1H NMR (400 MHz, DMSO-d6) delta 8.05 (d, J=8.7 Hz, 2 H), 8.12 (dd, J1=8.7 Hz, J2=1.4 Hz, 2 H), 8.85 (d, J=1.4 Hz, 2 H). Anal. (C14H6N2O.0.4H2O) C, H, N. 4,4′-Dibromo-2,2′-dinitrobiphenyl 14 [Moffatt, J. S. 3:6-Diamidinodibenzofuran. J. Chem. Soc. 1951, 625-62]. A suspension of 2,5-dibromonitrobenzene (13, 50.0 g, 178 mmol) and copper powder (100 mesh, 25.0 g, 391 mmol) in DMF (300 mL) was stirred at 137 C. (oil bath) under N2 for 2 h. The mixture was poured into toluene (1000 mL) and stirred for 4 h. Then the mixture was passed through Celite 545. The filtrate was collected and washed with water and dried over anhydrous sodium sulfate. The solvent was evaporated, and the residue was recrystallized from ethanol (650 mL) to give a pale yellow solid (31.33 g, 87.57%): m.p. 143-146 C. (reported 150 C. [Shaw, F. R.; J. Chem. Soc. 1932, 285-297] and 146-148 C. [Yamato, T.; et al., J. Org. Chem. 1991, 56, 6248-6250]); HPLC method 3 tR=18.70 min (97.2%); NMR (300 MHz, CDCl3) delta 8.40 (d, J=2.0 Hz, 2 H), 7.85 (dd, J1=8.2 Hz, J2=2.0 Hz, 2 H), 7.18 (d, J=8.2 Hz, 2 H).

The synthetic route of 10016-52-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The University of North Carolina at Chapel Hill; US6172104; (2001); B2;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 55289-36-6, 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. 55289-36-6, name is 3-Bromo-2-methylaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a flask containing aqueous sulfuric acid (14%, 260 mL), 3-bromo-2-methylaniline (5.00 mL, 40.6 mmol) was added. The mixture was brought to reflux, and a solution of sodium nitrite (3.08 g, 44.6 mmol) in water (minimum amount required to dissolve) was added dropwise over the course of 1 hour. The mixture was refluxed an additional 30 minutes, cooled to room temperature, and extracted three times with chloroform. The combined chloroform layeres were extracted three times with aqueous sodium hydroxide (1 M). The aqueous layers were acidified with concentrated hydrochloric acid and extracted three times with chloroform. These three chloroform extracts were combined, dried over magnesium sulfate, filtered, and concentrated to give 3-bromo-2-methylphenol (10-1, 5.63 g) as a brown solid.

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-2-methylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Aviara Pharmaceuticals, Inc.; Biediger, Ronald J.; Benish, Michele A.; Hardy, Lindsay Bonner; Boyd, Vincent A.; Market, Robert V.; Thrash, Thomas P.; Young, Brandon M.; (83 pag.)US2018/312523; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 22385-77-9,Some common heterocyclic compound, 22385-77-9, name is 1-Bromo-3,5-di-tert-butylbenzene, molecular formula is C14H21Br, 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 bromide (2.0 g, 7.4 mmol), tri-nbutyi-1-ethoxyvinyl tin (3.2 g, 8.9 mmol), and PdCl2(Ph3P)2 ( 522 mg, 0.74 mmol) were dissolved in toluene 3.7 mL and the solution stirred at 95 0C for 3 hours. The volatiles were removed in vac. and the residue dissolved in 1,4-dioxane (33 mL). Aqueous HCl (2 N, 1 1 mL) was added and the solution stirred rapidly at RT for 1 hour. The mixture was diluted with water (350 mL), followed by aqueous/EtOAc work-up and silica gel chromatography (diethyl ether: hexanes (1 :9)) to give the titled compound.

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

Reference:
Patent; MERCK & CO., INC.; WO2007/64553; (2007); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 22385-77-9, name is 1-Bromo-3,5-di-tert-butylbenzene, 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. Safety of 1-Bromo-3,5-di-tert-butylbenzene

Production Example 2 of Optically Active AminoalcoholA 200 mL round-bottom four-neck flask equipped with a Dimroth condenser with a nitrogen introducing tube attached thereto, a thermometer, a magnetic rotator and a dropping funnel was heated under reduced pressure, nitrogen was then introduced into the flask, pressure in the flask was returned to normal pressure, and the flask was cooled to room temperature. After 1.27 g of magnesium and a minor amount of iodine were added to the flask, a small amount of a solution obtained by mixing 15.00 g of 3,5-di-tert-butylbromobenzene and 75.0 mL of dehydrated tetrahydrofuran was added dropwise. The flask was heated, and it was confirmed that the Grignard reaction was initiated. Thereafter, the remaining solution was added dropwise to the flask over 30 minutes. The resulting mixture was refluxed for 1.5 hours. After the resulting reaction mixture was cooled to -10° C., 1.11 g of L-valine methyl ester hydrochloride was added. After the temperature of the resulting mixture was raised to room temperature, the mixture was further refluxed for 4 hours. The resulting reaction mixture was cooled to 0 to 5° C. To the reaction solution were added dropwise 45.0 mL of an aqueous saturated ammonium chloride solution, and further 15.0 mL of water. The resulting mixture was stirred at 20° C. for 30 minutes. The resulting mixture was extracted with 45.0 mL of diethyl ether three times. The resulting organic layers were mixed, and dried with anhydrous sodium sulfate. After sodium sulfate was removed by filtration, the resulting filtrate was concentrated. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=2/9840/60) to obtain 1.02 g of a colorless crystal of (S)-2-amino-1,1-di(3,5-di-tert-butylphenyl)-3-methyl-1-butanol.1H-NMR (300 MHz, CDCl3, TMS standard)delta (ppm): 7.54 (2H, d), 7.43 (2H, d), 7.28 to 7.24 (2H, m), 4.23 (1H, brs), 3.80 (1H, d), 1.77 (1H, m), 1.35 (18H, s), 1.33 (18H, s), 1.32 (2H, s), 0.96 (3H, d), 0.87 (3H, d)13C-NMR (75 MHz, CDCl3, TMS standard)delta (ppm): 150.86, 150.43, 147.46, 144.67, 121.01, 120.80, 120.76, 120.38, 81.24, 62.12, 35.67, 35.61, 32.33, 32.27, 28.60, 23.88, 17.09

The synthetic route of 1-Bromo-3,5-di-tert-butylbenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Masumoto, Katsuhisa; Yoshikawa, Kouji; US2011/166372; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 2635-13-4, 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. 2635-13-4 name is 5-Bromobenzo[d][1,3]dioxole, 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.

A heavy-walled tube was charged with 5.01 grams (3 ml, 24.896 mmol) ofcommercially available 5-bromo-1,3-benzodioxole followed by dry DMF (5ml) followed by copper iodide (0.474 grams, 2.490 mmol, 0.10 equivalents), PdCl2(PPh3)2 (0.349 grams, 0.4979 mmol, 0.02 equivalents), and triethylamine (35 ml) and then subjected tooxygen removal using a freeze-pump-thaw method. Finally TMS-acetylene (3.68 grams, 5.3 ml,37.34 mmol) was then added and the tube was quickly sealed and heated in an oil bath at 90 Cfor 24 hours. At this time the reaction was cooled and worked up by concentration in vacuo andsubmitted to flash chromatography using straight hexanes to afford compound weighing 3.4 g.Yield is 62 %.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromobenzo[d][1,3]dioxole, and friends who are interested can also refer to it.

Reference:
Article; Abrams, Jason N.; Zhao, Qi; Ghiviriga, Ion; Minaruzzaman; Tetrahedron; vol. 68; 2; (2012); p. 423 – 428;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 61326-44-1, The chemical industry reduces the impact on the environment during synthesis 61326-44-1, name is 1,1,2,2-Tetrakis(4-bromophenyl)ethene, I believe this compound will play a more active role in future production and life.

Using the polar solvent “one-pot synthesis”, the 1, 1, 2, 2-tetra (4-bromophenyl) ethylene, 1H-1, 2, 4-triazole, potassium carbonate, and copper oxide in the preparation of the heating condition; wherein the 1, 1, 2, 2-tetra (4-bromophenyl) ethylene: 1H-1, 2, 4-triazole: potassium carbonate: copper oxide in a molar ratio of 2:10-15 : 30:1; the reaction temperature 80-200°C, reaction time 12-120 hours. The present invention is preferably 1, 1, 2, 2-tetra (4-bromophenyl) ethylene: 1H-1, 2, 4-triazole: potassium carbonate: copper oxide in a molar ratio of 2:10-15 : 30:1; the reaction temperature is 100 °C, the reaction time is 48 hours. In the polar solvent, the “one-pot synthesis”, the 1, 1, 2, 2-tetra (4-bromophenyl) ethylene, 1H-1, 2, 4-triazole, potassium carbonate, and copper oxide under the heating condition preparing 1, 1, 2, 2-tetra [4 – (1H-1, 2, 4-triazole-1-yl) phenyl] ethylene (L). Yield 60percent

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, 1,1,2,2-Tetrakis(4-bromophenyl)ethene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Tianjin Normal University; Wang, yin; (12 pag.)CN105418655; (2016); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 1003-99-2, name is 2-Bromo-5-fluoroaniline, 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 1003-99-2, Safety of 2-Bromo-5-fluoroaniline

To a solution of 2-bromo-5-fluoroaniline (1.0 eq.) in tetrahydrofuran (0.2 M) at 0° C. under N2 atmosphere was added dropwise 1M NaHMDS (2.5 eq.). The reaction was stirred for 15 minutes at 0° C., and a solution of di-tert-butyl dicarbonate in tetrahydrofuran was added. The reaction was warmed to room temperature overnight. The solvent was evaporated, and the resulting residue was quenched with 0.1N HCl aqueous solution. The aqueous suspension was extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous MgSO4, and concentrated en vacuo. The crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-5percent ethyl acetate in hexane to give the product as light yellow oil.

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, 2-Bromo-5-fluoroaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GlaxoSmithKline Biologicals SA; Skibinski, David; Jain, Siddhartha; Singh, Manmohan; O’Hagan, Derek; (124 pag.)US9408907; (2016); B2;,
Bromide – Wikipedia,
bromide – Wiktionary

2695-47-8, name is 6-Bromo-1-hexene, 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. HPLC of Formula: C6H11Br

To a suspension of tosylamide (50.25 g, 293.5 mmol) and K2CO3 (17.28 g, 125.0 mmol) inDMSO (250 ml) was added 6-bromo-1-hexene (S3, 13.36 ml, 100.0 mmol) at room temperature.After stirring for 15 h at room temperature, the reaction mixture was filtered through a shortplug of Celite and partitioned between diethyl ether and H2O. The aqueous phases wereextracted twice with diethyl ether. The combined organic phases were washed with brine, driedover MgSO4, filtered and concentrated under reduced pressure. The residue was purified byflash column chromatography (20% EtOAc/hexane) to afford S4 (20.05 g, 78.15 mmol, 78%) asa yellow oil.

The synthetic route of 2695-47-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Orihara, Kensuke; Kawagishi, Fumiki; Yokoshima, Satoshi; Fukuyama, Tohru; Synlett; vol. 29; 6; (2018); p. 769 – 772;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 7499-66-3, The chemical industry reduces the impact on the environment during synthesis 7499-66-3, name is 6-Bromonaphthalen-2-amine, I believe this compound will play a more active role in future production and life.

According to a known method described in a reference [L. C. Anderson et al., Journal of the American Chemical Society (J. Am. Chem. Soc.), vol. 65, p.241, 1943], a solution of 2-amino-6-bromonaphthalene (223 mg) obtained from commercially available 2-bromo-6-hydroxynaphthalene (TCI) in anhydrous THF (10 ml) was added with 30percent potassium hydride (191 mg, Ald) under ice cooling and stirred for 1 hour. The reaction mixture was cooled to -78° C. under argon atmosphere, added dropwise with-1.7 M solution of t-butyllithium in pentane (1.88 ml) over 10 minutes and stirred for 30 minutes. The reaction mixture was added dropwise with (iPrO)3B (0.92 ml) over 10 minutes, stirred for 30 minutes, then warmed to room temperature and further stirred for 3 hours. The reaction mixture was added with water (3 ml) and 0.5 M aqueous sulfuric acid (4 ml) and extracted with diethyl ether (100 ml.x.3). The organic layer was washed with saturated brine and dried, and then the solvent was evaporated under reduced pressure to obtain crude 6-amino-2-naphthaleneboronic acid (402 mg). According to the procedure described in the synthesis method of Compound of Example 001 (Preparation Method 4, Step d-1) with the modifications that the reaction was carried out for 13 hours, and the purification was performed by flash column chromatography (hexane:ethyl acetate=4:1), a solution of the above compound in ethanol (0.5 ml), Intermediate 3 (119 mg), 2 M aqueous sodium carbonate (1.5 ml) and (Ph3P)4Pd (61 mg) were reacted and treated to obtain the title compound (Compound No. 011, 129 mg).

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, 6-Bromonaphthalen-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shoda, Motoshi; Kuriyama, Hiroshi; US2004/44258; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary