Author: Jessica.F

Electric Literature of 53078-85-6,Some common heterocyclic compound, 53078-85-6, name is 2-Bromo-5-methylaniline, molecular formula is C7H8BrN, 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.

To a solution of 5.0 g of 2-bromo-5-methylaniline in 17 ml of hydrochloric acid (37%) was added dropwise, at 0 C. within 30 minutes, a solution of 1.9 g of sodium nitrite in 9.6 ml of water. Subsequently, at 0 C., a solution of 16.6 g of tin chloride in 15 ml of hydrochloric acid (37%) was added dropwise, and the mixture was stirred at this temperature for a further 1.5 hours. After adding 60 ml of sodium hydroxide solution (50%) and 30 ml of ice-water (pH>10), the mixture was extracted three times with 500 ml each time of ether. The combined organic phases were washed with semisaturated sodium chloride solution and dried over sodium sulphate. The filtrate was acidified with 4.0M hydrochloric acid in 1,4-dioxane solution and the resulting precipitate was then filtered off and dried. Yield: 5.85 g of the title compound.NMR (300 MHz, DMSO-d6): delta=2.22 (3H), 6.70 (1H), 6.93 (1H), 7.39 (1H), 7.78 (1H), 10.29 (2H).

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-5-methylaniline, its application will become more common.

Reference:
Patent; Bayer Schering Pharma AG; US2010/29598; (2010); 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. 348-57-2, name is 1-Bromo-2,4-difluorobenzene, A new synthetic method of this compound is introduced below., Product Details of 348-57-2

1-Bromo-2,4-difluoro-5-nitrobenzene: To a 0° C. mixture of 1-bromo-2,4-difluorobenzene (20.0 g, 11.7 mL, 0.100 mol) and H2SO4 (76.8 mL) was added HNO3 (68.0 mL) over 45 min at such a rate that the internal temperature was <7° C. The resulting mixture was stirred for 1 h at 0° C., poured into ice water (400 mL), stirred vigorously for 2-3 min and extracted with CH2Cl2 (400 mL). The organic layers were washed with brine (1.x.500 mL), dried over Na2SO4, filtered and evaporated to give the product as a yellow oil (23.5 g, 95percent yield). 1H NMR (CDCl3) delta 8.39 (t, J=7.2 Hz, 1H), 7.14 (ddd, J=0.3, 7.8, 9.9 Hz, 1H). 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; H. Lundbeck A/S; US2006/79524; (2006); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 699-03-6,Some common heterocyclic compound, 699-03-6, name is 1-(4-Bromophenyl)-N-methylmethanamine, 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.

A mixture of l-(4-bromophenyl)-N-methylmethanamine (2 g, 10 mmol, 1.0 eq), TEA (3 g, 30 mmol, 3 eq) was cooled to 0 C. Then acetyl chloride (942 mg, 12 mmol, 1.2 eq) in DCM (20 mL) was added. The mixture was stirred at rt for 1 h. The mixture was washed with brine,dried over Na2SO i, filtered and concentrated. The residue was purified on silica gel column (PE/EtOAc = 5/1) to give N-(4-bromobenzyl)-N-methylacetamide as a yellow oil (1.6 g, 67%).

The synthetic route of 699-03-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LIFESCI PHARMACEUTICALS, INC.; MCDONALD, Andrew; WO2015/103317; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 1435-52-5, 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. 1435-52-5, name is 1,4-Dibromo-2-fluorobenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

150ml three-necked flask, Add 0.01 mol of 2,5-dibromofluorobenzene, 0.012 mol of M5, 0.02 mol of sodium carbonate and 10 ml of ethylene glycol dimethyl ether, It was purged with nitrogen, heated to 190 ° C, and stirred for 48 hours. Then cooled to room temperature and poured into a beaker. Add 50 ml of toluene and 50 ml of water and stir for 20 minutes. Filtration, the filtrate is steamed, passed through a silica gel column, Obtaining a white intermediate 7a, The purity was 98.10percent, and the yield was 70.5percent.

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, 1,4-Dibromo-2-fluorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Jiangsu March Optoelectric Technology Co., Ltd.; Ye Zhonghua; Zhang Zhaochao; Li Chong; Zhang Xiaoqing; (57 pag.)CN109575057; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 1073-06-9, 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. 1073-06-9, name is 1-Bromo-3-fluorobenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example A-3 4-(3-Fluoro-phenyl)-1H-indole To a mixture of 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole (3, 2.43 g, 10 mmol), and 3-bromofluorobenzene (1.09 mL, 10 mmol) in THF (34 mL)) were added Palladium catalyst Pd(PPh3)4 (347 mg, 0.3 mmol) and the freshly prepared sodium hydroxide solution (1.20 g, 30 mmol in 14 mL water). The system was degassed and then charged with nitrogen. The degas procedure was repeated for three times. The mixture was stirred under nitrogen at 70 C. oil bath for 15 hours. TLC showed the completion of the coupling reaction. The mixture was cooled to room temperature, diluted with ethyl acetate, and separated from water layer. The ethyl acetate solution was washed by brine, dried over Na2SO4, and concentrated. The crude product was purified by a silica gel column eluding with hexanes-EtOAc (9:1) to provide 1.88 g (88%) of the product 4-(3-fluoro-phenyl)-1H-indole as a colorless syrup. 1H-NMR (400 MHz, DMSO-d6) delta 11.30 (br s, 1H, NH), 7.52 (m, 2H, aromatic), 7.45 (m, 3H, aromatic), 7.20 (m, 2H, aromatic), 7.12 (m, 1H, aromatic), 6.55 (m, 1H, aromatic). MS m/z 212 [M++1].

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-3-fluorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sugen, Inc.; US2003/69297; (2003); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 134168-97-1, name is 3-Bromo-5-fluoroaniline, molecular formula is C6H5BrFN, 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. category: bromides-buliding-blocks

1000mL 4 neckround bottom flask was charged with 3-bromo-5-fluoroaniline 30.5 g (0.16 mole) and Pd (PPh3) 47.4 g (0.006mole) of potassium carbonate and 88.1 g (0.64 mole) and 1naphthylboronic acid put 32.7 g (0.19 mole), toluene was putinto 210 mL, 160 mL ethanol, 90 mL of water was refluxed for 12 hours. To complete the reaction, and the organic layer wasseparated and the water layer was extracted twice with 100 mL toluene. Formed organic layer was concentrated underreduced pressure and recrystallized with methanol to intermediate a3(27.4 g, 72.1%) was obtained.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 134168-97-1, its application will become more common.

Reference:
Patent; SFC CO., LTD.; KIM, JEONG SOO; RYU, YEON KWON; KO, SANG WON; LEE, SU JIN; KIM, JI HWAN; PARK, JIN JOO; (44 pag.)KR2015/129486; (2015); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 75024-22-5, These common heterocyclic compound, 75024-22-5, name is 1,4-Dibromo-2,3-dimethylbenzene, 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.

Add 6.3 mmol to a 100 ml three-necked flask under N2 protection.1,4-Dibromo-2,3-dimethylbenzene, 13.5 mmol 3,5-dimethylphenylboronic acid25.6mmol potassium carbonate, 0.2mmol tetrakistriphenylphosphine palladium,30 ml of 1,4-dioxane, 6 ml of deionized water, and then replaced with nitrogen three times.Then, it was heated to 90 C with an oil bath under magnetic stirring for 6 h. After the reaction,After washing with water, extracting, drying, and removing the organic solvent under reduced pressure,The product was isolated by column chromatography (petroleum ether), yield 88%.1.9 mmol of the obtained product, 68 mmol of potassium permanganate, 10 ml of pyridine,12 ml of distilled water was added to a 100 ml three-necked flask, and then heated to 100 C with an oil bath under magnetic stirring, and the reaction was refluxed for 15 hours. After the reaction was completed, the organic solvent was depressurized under reduced pressure, and then water was added thereto. After ultrasonic etching, MnO 2 was filtered through celite.Adding hydrochloric acid to adjust the pH to 1 can precipitate a large amount of white powder, collect by centrifugation and dry.The polycarboxylic acid product was obtained in a yield of 94%.Finally, 1.8 mmol of hexacarboxylic acid product, 4 mmol of hydroxylamine hydrochloride,10 ml of pyridine was added to a 50 ml single-necked flask and heated to 90 C with an oil bath under magnetic stirring.Reaction for 6 h. After the reaction, the organic solvent was depressurized under reduced pressure, and then diluted with hydrochloric acid for a while, collected by centrifugation and dried to obtain an off-white product b with a yield of 97%.

Statistics shows that 1,4-Dibromo-2,3-dimethylbenzene is playing an increasingly important role. we look forward to future research findings about 75024-22-5.

Reference:
Patent; Tongji University; Li Liangchun; Liang Gan; Sun Chengmei; (12 pag.)CN109608381; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 101417-40-7, 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. 101417-40-7 name is 4-(Bromomethyl)benzo[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.

5.8 g (0.025 mol) of Va, 3.3 g (0.027 mol) of p-hydroxybenzaldehyde,10.2 g (0.076 mol) of potassium carbonate and 1 g of potassium iodide were added to 40 ml of acetone and the reaction was refluxed overnight.Stop the reaction, filter, evaporate the solvent under reduced pressure, add ethyl acetate and water, and separate the liquid.The aqueous phase was extracted with ethyl acetate and the organic phases were combined, washed with saturated brine and dried over anhydrous sodium sulfate for 8 hours.The desiccant was filtered off, the solvent was evaporated under reduced pressure, and the residue was separated by silica gel column chromatography.Elution with petroleum ether:ethyl acetate (10:1) to collect the desired components,VIb white solid 5.1g, yield 78.2%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-(Bromomethyl)benzo[d][1,3]dioxole, and friends who are interested can also refer to it.

Reference:
Patent; The Chinese People’s Liberation Army Military Academy Of Medical Sciences Poison Pharmaceutical Institute; Zhong Bohua; Zhang Ping; He Xinhua; Shi Weiguo; Fan Shiyong; Yao Yishan; Jia Hongxin; (20 pag.)CN103804341; (2018); B;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 156682-52-9,Some common heterocyclic compound, 156682-52-9, name is 1,4-Dibromo-2,3-difluorobenzene, molecular formula is C6H2Br2F2, 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.

-PrMgCl-LiCl (2 M, 2.03 mL) at -40C was added to a solution of Compound BD4-3 (0292) (1.00 g, 3.68 mmol) in THF (20.00 mL) at -40C. The mixture was stirred at -40C for 1 hour and again stirred at -7C for another 1 hour. The mixture was then cooled to -30C. DMF (349.66 mg, 4.78 mmol) at -23C was added in one portion. The mixture was stirred while keeping a temperature range of -25C to 15C for 3.5 hour. TLC indicated when the reaction was completed. The reaction mixture was poured into H2SO4 (100 mL, 1M) cooled to 0C by ice bath, and then the resulting mixture was extracted with EtOAc (20 mL * 3). The combined organic layers of the reaction mixture were washed with brine (30 mL * 3), dried over Na2SC>4, filtered and concentrated under reduced pressure to afford Compound BD4-4 (800.00 mg, crude) as a yellow solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,4-Dibromo-2,3-difluorobenzene, its application will become more common.

Reference:
Patent; THE BROAD INSTITUTE, INC.; VACCA, Joseph, P.; (103 pag.)WO2018/75871; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

16518-62-0, name is 3-Bromo-N,N-dimethylaniline, 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: C8H10BrN

General procedure: Bromo-N,N-dimethylaniline (400 mg, 2.0 mmol), (trimethylsilyl)acetylene (236 mg, 2.4 mmol), Pd(PPh3)4 (116 mg, 0.1 mmol), CuI (19mg, 0.1 mmol), diisopropylamine (5 mL) and toluene (15 mL) wereadded to a flask and the mixture was stirred at 80 C overnight. Thenthe reaction mixture was poured into saturated NH4Cl (50 mL) andextracted with CH2Cl2 (3 x 20 mL), the organic layer was washed withsaturated brine (1 x 50 mL) and dried over MgSO4. After filtration,solvents were removed by rotary evaporation (40-45 C ). The crudeproduct was subjected to column chromatography (SiO2; eluent,hexane/ CH2Cl2, 3:1) to give the corresponding compounds. N,N-Dimethyl-3-[(trimethylsilyl)ethynyl]aniline (3b): Pale yellow oil; yield 84%.

The synthetic route of 16518-62-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Fang, Jing-Kun; Sun, Tengxiao; Fang, Yu; Xu, Zhimin; Zou, Hui; Liu, Yuan; Ge, Fangting; Journal of Chemical Research; vol. 39; 8; (2015); p. 487 – 491;,
Bromide – Wikipedia,
bromide – Wiktionary