Bromides-buliding-blocks

Electric Literature of 1435-53-6,Some common heterocyclic compound, 1435-53-6, name is 2,4-Dibromo-1-fluorobenzene, molecular formula is C6H3Br2F, 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.

Mix 4g (23.1 mmol) of intermediate B, 6.4 g (25.4 mmol) of 2,4-bromo-1-fluorobenzene (2,4-Bromo-2-Fluorobenzene), 11.3 g (34.6 mmol) cesium carbonate and 80 ml DMF, and placed under nitrogen, followed by heating at 150CStir for 12h. After the reaction was completed, the mixture was allowed to cool to room temperature. The solution was extracted with 250 ml of ethyl acetate and 300 ml of water. organicThe layer was dried using anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtainWhite solid product (7.8 g, 19.2 mmol, yield: 83.1%).

The synthetic route of 1435-53-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiguang Technology Co., Ltd.; Yan Fengwen; (56 pag.)CN107739382; (2018); A;,
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Related Products of 103-64-0,Some common heterocyclic compound, 103-64-0, name is (2-Bromovinyl)benzene, molecular formula is C8H7Br, 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 N, N-dimethylformamide (DMF) in a volume ratio of 4: 1 with polyethylene glycol 200(PEG-200)) was added 100 mmol of the compound of the above formula (I), 60 mmol of the compound of the above formula (II), 8 mmol of catalyst bis (triphenylphosphine) cyclopentadienyl ruthenium chloride, 120 mmol of an oxidizing agent bis Fluoroacetic acid) iodobenzene (PhI (TFA) 2),15 mmol of organic ligands L1 and 80 mmol of base, 5,7-triazabicyclo [4.4.0] dec-5-ene (TBD) were added and the mixture was allowed to warm to 80 C with stirring and the reaction was stirred at that temperature for 11 hours; After completion of the reaction, the reaction system is naturally cooled to room temperature and the pH is adjusted to neutral, filtered and the filtrate is saturatedWashed with brine and extracted with ethyl acetate 2-3 times. The organic phases were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography at a 1: 2 by volume mixture of chloroform and petroleum ether Followed by elution to give the compound of formula (III) in a yield of 94.8%.

The synthetic route of 103-64-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Huang, Cheng; No proclaimed inventor; (12 pag.)CN106278839; (2017); A;,
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1003-99-2, name is 2-Bromo-5-fluoroaniline, 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. name: 2-Bromo-5-fluoroaniline

1-(5-fluoroquinolin-8-yl)piperidin-4-one (Example P, Step 3) is also prepared as shown in the reaction scheme above. To a 500 ml flask equipped with a stirrer, a thermocouple, a condenser and nitrogen inlet were charged 50 g 2-bromo-5-fluoroaniline and 60 g glycerol. The mixture was heated to 60¡ã C. and 55 g nitrobenzene sulfonic acid was charged in portion. The mixture was then heated to 100-110¡ã C., started charge 200 ml 70percent sulfuric acid. After sulfuric acid addition, the mixture was heat to 130¡ã C. and stirred for 3 hours before cooled to room temperature. Water (300 g) was added and a grayish by product was filtered off. The filtrate was slowly added into a 2-L reactor containing a mix of 420 g 50percent NaOH, 420 g of water, 352 g methyl tert-butyl ether. After filtering off small amount solid, the aqueous layer was split off and the organic layer was washed with 10percent NaOH (2.x.100 ml), 20percent NaCl (2.x.200 ml), the solvent was removed, weight 56 g, 89.8percent.

The synthetic route of 1003-99-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wyeth; US2007/27160; (2007); A1;,
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Adding a certain compound to certain chemical reactions, such as: 348-57-2, name is 1-Bromo-2,4-difluorobenzene, 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 348-57-2, Recommanded Product: 1-Bromo-2,4-difluorobenzene

Preparation 131 ,5-dibromo-2,4-difluorobenzeneTo a solution of l-bromo-2,4-difluorobenzene (19.3 mL, 171 mmol) in CH2CI2 (100 mL) was added iron (3.15 g,56 mmol). To this stirred suspension was added a solution of bromine (1 1 mL, 214 mmol) in CH2CI2 (25 mL) drop wise over 30 min. The resulting mixture was stirred at rt overnight. The reaction mixture was slowly poured into saturated aqueous Na2S203 (200 mL), and the resulting mixture was stirred at rt for 30 min. This was extracted with CH2C12 (3 x 80 mL). The combined extracts were washed with brine, dried over MgS04, filtered and concentrated in vacuo to give 1,5-dibromo- 2,4-difluorobenzene (40 g, 86 % yield) as a brown oil. XH NMR (500 MHz,CHLOROFORM-d) delta 7.79 (t, J=7.0 Hz, 1H), 7.00 (t, J=8.2 Hz, 1H).

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-2,4-difluorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WU, Yong-Jin; WO2012/162334; (2012); 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. 1435-52-5, name is 1,4-Dibromo-2-fluorobenzene, A new synthetic method of this compound is introduced below., Quality Control of 1,4-Dibromo-2-fluorobenzene

150ml three-necked flask, add 0.01 mol of 2,5-dibromofluorobenzene, 0.012 mol M1, 0.02 mol sodium carbonate and 10 ml ethylene glycol dimethyl ether, It was purged with nitrogen, heated to 190 ¡ã 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 white intermediate 1a, The purity was 98.60percent, and the yield was 80.5percent.

The synthetic route of 1435-52-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu March Optoelectric Technology Co., Ltd.; Ye Zhonghua; Zhang Zhaochao; Li Chong; Zhang Xiaoqing; (57 pag.)CN109575057; (2019); A;,
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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. 452-74-4, name is 1-Bromo-2-fluoro-4-methylbenzene, A new synthetic method of this compound is introduced below., Product Details of 452-74-4

Step 3: Preparation of l-bromo-4-(bromomethyl)-2-fluorobenzene; To a room temperature solution of 4-bromo-3-fluorotoluene (10.6 g) in 150 mL of carbon tetrachloride were added benzoyl peroxide (100 mg ) and N-bromosuccinimide (10 g). The mixture was heated at 800C (with shine light) for 4 hours. The reaction mixture was cooled to 00C and filtered through celite, washed with hexanes and the solvent removed in vacuo. The crude material was purified by chromatography on SiO2 using hexanes to yield the title compound containing -30 % of 1- bromo-4-(dibromomethyl)-2-fluorobenzene as impurity.1H NMR (CD3COCD3) delta 7.66-7.10 (1 H, m), 7.42 (1 H, d), 7.29 (1 H, d), 4.66 (2 H, s).

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; MERCK FROSST CANADA LTD.; WO2006/133559; (2006); A1;,
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Application of 74586-53-1, 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. 74586-53-1, name is 3-Bromo-5-methylaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Add m-bromoaniline (688mg, 4mmol), intermediate 3-2 (940mg, 5mmol), cuprous iodide (10%), L-proline (L-Pro, 20%) to a 25ml Shrek tube. , Cesium carbonate (2equiv) and dimethyl sulfoxide (0.5M). The resulting mixture was sparged with nitrogen for 10 minutes and stirred at 120 C for 3 days. After cooling, water and ethyl acetate (EA) were added, and the mixture was filtered. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined, washed with brine, and the organic phase was dried over anhydrous Na2SO4. Using PE: EA = 10: 1 as the eluent, the obtained solution was purified by silica gel chromatography to obtain intermediate 3-3 (brown viscous liquid, yield 75%).

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

Reference:
Patent; Nanjing Jianuolin Optoelectric Technology Co., Ltd.; Hang Xiaochun; Yin Junli; Wang Ying; (66 pag.)CN110551157; (2019); A;,
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Reference of 100189-84-2, 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. 100189-84-2, name is 2,5-Dibromo-1,3-dimethylbenzene, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 2,5-dibromo-1,3-dimethylbenzene (2640 mg, 10 mmol, Oakwood Products, Inc. – 018507) in anhydrous acetonitrile (25 mL) was added palladium(U) acetate (112 mg, 0.5 mmol), acrylonitrile (531 mg, 10 mmol), tri(o-tolyl)phosphine (131 mg, 0.5 mmol) and triethylamine (4 mL, 30 mmol) then the mixture was purged with argon and heated at 110 C for 2 hours. The reaction mixture was filtered through Celite and the filter pad was washed with tetrahydrofuran (10 mL). The filtrate was evaporated then re-dissolved with ethyl acetate (50 mL). The solution was washed with water (50 mL). The water layer was back extracted with ethyl acetate (50 mL). The combined organics were washed with brine (30 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure to give a crude residue. This was subjected to silica gel chromatography (gradient from 0-20% ethyl acetate in iso-hexanes) to afford the crude product which was treated in sonic bath with hexane (10 mL) for 10 minutes. The product precipitated out of solution and was collected by filtration. The solids were washed with cold hexane to afford compound id. ?H NMR (400 MHz, CDC13) 67.25 (d,J= 16.6 Hz, 1H), 7.12 (s, 2H), 5.84 (d,J 16.6 Hz, 1H), 2.42 (s, 6H). LCMS (mlz) no MS signal, Tr = 2.78 mm (LCMS method 1).

The chemical industry reduces the impact on the environment during synthesis 2,5-Dibromo-1,3-dimethylbenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; GILEAD SCIENCES, INC.; JANSA, Petr; MACKMAN, Richard, L.; HU, Yunfeng, Eric; LANSDON, Eric; (81 pag.)WO2016/105534; (2016); A1;,
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Application of 15155-41-6, 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. 15155-41-6, name is 4,7-Dibromo-2,1,3-benzothiadiazole belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

4,7-Dibromo-2,1,3-benzothiadiazole (12.204 g, 42.5 mmol) was added to a 500 ml three-neck round bottom flask, dissolved in 400 ml of absolute ethanol, passed through a nitrogen atmosphere, and cooled to 0 C. NaBH4 (15.69 g, 425 mmol) was added portionwise to the solution. After the addition of NaBH4, the reaction mixture was transferred to room temperature overnight. The reaction solution was poured into a beaker, and the solid precipitated in the bottle was completely dissolved by adding 50 ml of water. The large amount of ethanol in the bottle was removed, extracted with dichloromethane and water, and the combined organic phases were washed with water, dried over anhydrous magnesium sulfate and filtered.The filtrate was distilled under reduced pressure to give a pale yellow solid (7.583 g, 28.74 mmol, 67.6%).That is, 3,6-dibromo-1,2-phenylenediamine, the structural formula is:

The synthetic route of 4,7-Dibromo-2,1,3-benzothiadiazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangxi Normal University; Liang Aihui; Zhou Wenjing; Xie Qi; Zhang Jiayu; Liu Zhiqian; Hu Sifan; (26 pag.)CN110204561; (2019); A;,
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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. 454-79-5, name is 2-Bromo-5-(trifluoromethyl)aniline, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Bromo-5-(trifluoromethyl)aniline

Reference Example 94 Synthesis of 2-(2-methyl-6-trifluoromethyl-1H-indol-3-yl)acetic acid A mixture of 3-amino-4-bromobenzotrifluoride (1.2 g), levulinic acid (1.0 g), p-TsOH (0.1 g) and benzene (10 ml) was heated to reflux for 3 hours using a Dean Stark tube. The reaction mixture was concentrated under reduced pressure, and a mixture of palladium acetate (60 mg), tris(o-tolyl)phosphine (0.15 g), triethylamine (0.8 g) and DMF (2 ml) was stirred with the obtained residue in a sealed tube for 20 hours at 120 C. Water and ethyl acetate were added to the reaction mixture, the insoluble portion was filtered out with celite and extraction was performed with ethyl acetate, and then after combining the organic layer and drying over sodium sulfate, the product was concentrated under reduced pressure. Methanol (20 ml) and concentrated sulfuric acid (1 ml) were added to the obtained residue and the mixture was heated to reflux for 2 hours. Water was added to the reaction mixture, which was then extracted with dichloromethane, dried over sodium sulfate and concentrated under reduced pressure. 2-(2-methyl-6-trifluoromethyl-1H-indol-3-yl)acetic acid methyl ester was purified from the obtained residue by silica gel column chromatography using a mixed solvent of hexane and dichloromethane. A 2 N sodium hydroxide aqueous solution (1 ml) and methanol (1 ml) were added to the obtained 2-(2-methyl-6-trifluoromethyl-1H-indol-3-yl)acetic acid methyl ester, and the mixture was heated to reflux for one hour. Water was added to the reaction mixture, which was then rendered acidic with concentrated aqueous hydrochloric acid, extracted with ethyl acetate, dried over sodium sulfate and concentrated under reduced pressure, to obtain 79 mg of the title compound as a colorless powder (6% yield). The NMR data for the obtained compound were as follows. NMR: (300 MHz, DMSO-d6) delta: 2.38 (3H,s), 3.62 (2H,s), 7.23 (1H,dd), 7.5-7.7 (2H,m), 11.32 (1H,s), 12.0-12.4 (1H,m)

The synthetic route of 454-79-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Fujiwara, Shinya; Ozaki, Tomokazu; Kozono, Toshiro; Hattori, Kunihiro; Esaki, Toru; US2003/162724; (2003); A1;,
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