Tag: M.W=100-200

Reference of 4333-56-6, 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. 4333-56-6, name is Bromocyclopropane belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Tert-butyl N-ftert-butoxycarbonylamino)-N-cvclopropyl-carbamate To a stirred suspension of magnesium (1.34g, 55mmol) and catalytic iodine in tetrahydrofuran (5ml)was added 5ml of a 45ml solution of cyclopropyl bromide (4.0ml) in tetrahydrofuran (50ml). The mixture was heated to initiate Grignard formation then the remaining solution of cyclopropyl bromide was added dropwise over 30mins with heating (70C). The Grignard solution was heated at reflux for a further 30 minutes then cooled to 0C. To a stirred solution of di-tert-butyl azodicarboxylate in THF (50ml) at -78C was added the solution of cyclopropylmagnesium bromide dropwise via cannula. The resulting solution was stirred at -78C for 30mins then quenched with acetic acid. The mixture was allowed to warm to room temperature then water (150 ml) was added and the mixture extracted three times with diethyl ether. The combined organic extracts were dried, filtered and concentrated in vacuo. The crude product was purified by column chromatography on silica, eluting with ethyl acetate/hexane, to give the product as a white solid (6.68g). IH NMR (400 MHz, Chloroform) delta ppm 0.7 (4H, br s), 1.5 (18H, s), 2.9-3.0 (IH, br m), 6.1 and 6.4 (IH, br s)

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

Reference:
Patent; SYNGENTA LIMITED; BHONOAH, Yunas; ELLIOTT, Alison Clare; GAULIER, Steven; LING, Kenneth; MITCHELL, Glynn; MORRIS, James Alan; RZEPA, Paula Rocha; VINER, Russell Colin; WO2013/50421; (2013); A1;,
Bromide – Wikipedia,
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Related Products of 656-64-4, The chemical industry reduces the impact on the environment during synthesis 656-64-4, name is 3-Bromo-4-fluoroaniline, I believe this compound will play a more active role in future production and life.

Step 1: To 3-bromo-4~fluoroaniline (0.76 g, 4.0 mmol) and 2-chloro-4-(trifluoromethyl)pyrimidine (0.73 g, 4.0 mmol) was added dioxane (13.33 mL) and p-TSA (0.761 g, 4.0 mmol). The reaction was sealed and was heated at reflux overnight The reaction was cooled to room temperature and was diluted with ethyl acetate, washed with saturated aqueous NaHC03, and the organic was dried over sodium sulfate and filtered before concentration. The crude product was purified by flash chromatography (25:75 ethyl acetate: hexanes) to afford N- (3-bromo-4-fluoiOphenyl)-4-(trifluoromethyl)pyrimidin-2-amine (1.2 g, 3.57 mmol, 89%) as a pale yellowish solid. NMR (500 MHz, CDCI3): delta 8.68 (d, J – 4.9 Hz, 1 H); 7.99-7.96 (m, 1H); 7.51 (d, J= 8.4 Hz, 1 H); 7.29 (s} 1 H); 7.14 (t, J- 8.5 Hz, 1 H); 7.10 (d, J= 4.9 Hz, 1 H). rhSYK activity = +

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; MERCK CANADA INC.; ALTMAN, Michael, D.; ANDRESEN, Brian, M.; ARRINGTON, Kenneth, L.; CHILDERS, Kaleen Konrad; DI FRANCESCO, Maria Emilia; DONOFRIO, Anthony; ELLIS, John Michael; FISCHER, Christian; GUERIN, David Joseph; HAIDLE, Andrew, M.; KATTAR, Solomon; KNOWLES, Sandra Lee; LI, Chaomin; LIM, Jongwon; MACHACEK, MIchelle, R.; NORTHRUP, Alan, B.; O’BOYLE, Brendan, M.; OTTE, Ryan, D.; PETROCCHI, Alessia; REUTERSHAN, Michael, H.; ROMEO, Eric; SIU, Tony; TAOKA, Brandon, M.; TROTTER, B. Wesley; ZHOU, Hua; BURCH, Jason; COTE, Bernard; DUPONT-GAUDET, Kristina; FOURNIER, Jean-Francois; GAUTHIER, Jacques Yves; GUAY, Daniel; ROBICHAUD, Joel, S.; GRIMM, Jonathan; MADDESS, Matthew, L.; SCHELL, Adam, J.; SPENCER, Kerrie, B.; WOO, Hyun Chong; BHAT, Sathesh; WO2011/75515; (2011); A1;,
Bromide – Wikipedia,
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Related Products of 33786-90-2, 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. 33786-90-2, name is 5-Bromobenzene-1,3-diamine, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a mixture of 5-substituted-2,4-dichloropyrimidines 1a-j (1.00g, 5.52mmol) and benzene-1, 3-diamines 2a-j (0.59g, 5.52mmol) was dissolved in n-butanol (10mL) and DIPEA (1.42g, 11.04mmol) was added and the reaction mixture was stirred at room temperature. The reaction was continued until complete consumption of starting material, monitored by TLC, for 2?8h. The solvent was removed under reduced pressure and the residue was dissolved in EtOAc. Organic layer was washed with water, dried over Na2SO4 and evaporated to dryness. The residue was purified by flash column chromatography (SiO2, Hexanes/EtOAc) to afford the compounds 3a-j.

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

Reference:
Article; Addepalli, Yesu; Yang, Xiaohong; Zhou, Minghui; Reddy, D. Prabhakar; Zhang, Shao-Lin; Wang, Zhen; He, Yun; European Journal of Medicinal Chemistry; vol. 151; (2018); p. 214 – 225;,
Bromide – Wikipedia,
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17247-58-4, name is (Bromomethyl)cyclobutane, 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: C5H9Br

4-(4,455-tetramethyl-1 3,2-dioxaborolan-2-yl)-1H-pyrazole (2.00 g, 10.3 mmol), (bromomethyl)cyclobutane (3.5 ml, 31 mmol) and potassium carbonate (5.70 g, 41 .2 mmol) were stirred in N,N-dimethylacetamide (16 ml) overnight at 80C. The mixture was concentrated under reduced pressure, the residue was dissolved with ethyl acetate, and the resulting solution was washed three times with water. The combined organic layers were dried over a silicone filter and concentrated under reduced pressure to give 2.40 g (90 % purity, 80 % yield) of the title compound. LC-MS (Method 2): Rt = 1 .21 min; MS (ESIpos): m/z = 263 [M+H]+ 1H-NMR (400MHz, DMSO-d6): _ [ppm]= 1.24 (s, 12H), 1 .67 – 1 .99 (m, 6H), 2.67 – 2.77 1H), 4.12 (d, 2H), 7.55 (s, 1H), 7.90 (d, 1H).

The synthetic route of 17247-58-4 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,
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Reference of 38573-88-5, A common heterocyclic compound, 38573-88-5, name is 1-Bromo-2,3-difluorobenzene, molecular formula is C6H3BrF2, 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.

EXAMPLE 52 6-(2,3-Difluorophenyl)-1,2-dihydro-2,2,4-trimethylquinoline (Compound 152, structure 4 of Scheme II, where R1 =2,3-difluorophenyl) This compound was prepared according to General Method 2 (EXAMPLE 9) from Compound 9 (28.7 mg, 0.09 mmol) and 1-bromo-2,3-difluorobenzene (10 muL, 0.09 mmol, Aldrich). The crude product was isolated and purified by silica gel chromatography (75 mL silica, 5percent ethyl acetate/hexane) to afford 16 mg (62percent) of Compound 152. Data for Compound 152: 1 H NMR (400 MHz, acetone-d6) 7.21 (m, 5H); 6.57 (d, J=8.3, 1 H); 5.37 (s, 1H); 1.99 (s, 3H); 1.28 (s, 6H).

The synthetic route of 38573-88-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ligand Pharmaceuticals Incorporated; US5693646; (1997); 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. 10269-01-9, name is (3-Bromophenyl)methanamine, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C7H8BrN

General procedure: 4.2 General procedure to oxazoles from chalcone and benzylic amine: Under O2, a mixture of chalcone (0.2 mmol), benzylamine (0.4 mmol), CuBr2 (20 mol%), pyridine (0.4 mmol), K2CO3 (0.1 mmol), and LiBr (0.5 mmol) in dry toluene (2 mL) was refluxed at 110 C for 11 h. After the completion of the reaction, as monitored by TLC, the solvent was concentrated under vacuum and the residue was purified by flash column chromatography through silica gel (300-400 mesh) with petroleum ether/EtOAc as eluant to give the desired product.

According to the analysis of related databases, 10269-01-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Liu, Dongfang; Yu, Jintao; Cheng, Jiang; Tetrahedron; vol. 70; 6; (2014); p. 1149 – 1153;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 7073-94-1, A common heterocyclic compound, 7073-94-1, name is 1-Bromo-2-isopropylbenzene, molecular formula is C9H11Br, 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 suspension of dihydroisoquinolinone 8 (2.0 mmol), aryl/heteroaryl bromide (3.0 mmol), palladium acetate (0.2 mmol) and BINAP (0.2 mmol) in dioxane (10.0 mL) was degassed with argon. Then sodium tert-butoxide (3.0 mmol) was added. The reaction mixture was heated at 100 C under argon for 1 h, and then it was cooled to room temperature, quenched with ammonium chloride, and extracted with EtOAc. The organic extract was washed with brine, dried over sodium sulfate, and concentrated in vacuo. The crude material obtained was purified by silica-gel flash column chromatography to give the desired dihydroisoquinolinone 9.

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; Hu, Min; Guzzo, Peter R.; Zha, Congxiang; Nacro, Kassoum; Yang, Yuh-Lin; Hassler, Carla; Liu, Shuang; Tetrahedron Letters; vol. 53; 7; (2012); p. 846 – 848;,
Bromide – Wikipedia,
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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. 399-94-0, name is 1-Bromo-2,5-difluorobenzene, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1-Bromo-2,5-difluorobenzene

Concentrated sulfuric acid (57 mL) was cooled inan ice bath, and 69% nitric acid (25.5 g, 279 mmol) was added dropwise over 25minutes to prepare a mixed acid. To this mixed acid, under ice-cooling, dichloroethane(125mL) solution of 2-bromo-1,4-difluoro-benzene (50g, 254mmol) was droppedslowly over a period of 1.5 hours. After completion of the dropwise addition,the reaction solution was further stirred for 2 hours at room temperature.After completion of the reaction, the reaction solution was added in portionsto ice-water (500 g), then extracted with ether (300mL × 2). The organic layerwas washed successively with water (300mL), saturated aqueous sodium hydrogencarbonate solution (300mL), saturated brine (300mL), and then dried overanhydrous magnesium sulfate, and the solvent was evaporated under reducedpressure. The resulting crude product was purified by silica gel chromatography(hexane: chloroform = 4/1) to give a pale yellow solid of 1-bromo-2,5-difluoro-4-nitrobenzene(56 g, yield: 93% ).

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 399-94-0.

Reference:
Patent; SAGAMI CHEMICAL RESEARCH INSTITUTE; KAKEN PHARMACEUTICAL COMPANY LIMITED; KOBAYASHI, OSAMU; TAKATSUNA, REIKO; NIIKURA, NAOKO; MATSUKAWA, TOMOKO; NAKAMURA, SHINJI; HIRAI, KENJI; KOCHI, SHINICHIRO; KAWANISHI, NAOKI; YAMADA, OSAMU; (75 pag.)JP2016/56157; (2016); A;,
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. 65896-11-9, name is 2-Bromo-6-fluoroaniline, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Bromo-6-fluoroaniline

Preparation of intermediate 3A:N-(4-bromophenyl)-4-fluorobenzothiazol-2-ylamine2-Bromo-6-fluoroaniline (500 mg, 2.63 mmol) and potassium carbonate (5726 mg, 5.26 mmol) were placed in a flask, to which was added 10 mL of DMSO. l-Bromo-4-thiocyanato-benzene (845 mg, 3.95 mmol) was added under nitrogen protection and resulting mixture was stirred at room temperature for 30 min. Cuprous iodide (50 mg, 0.263 mmol) was added and then heated to 120 C under nitrogen protection, and reacted overnight. The mixture was cooled to room temperature, poured into water to give a precipitate, which was filtered to give 383 mg of compound 3 A, which was used directly in the next step without further purification. Yield: 45.2%.MS (ESI, m/z): [M+H]+: 324.0

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; BEIJING HANMI PHARMACEUTICAL CO., LTD; ZHANG, Bo; YANG, Jun; LIU, Jinming; HUANG, Hai; WU, Yong; TAO, Ran; XU, Jiangcheng; SHEN, Ning; MOON, Sunghwan; KIM, Maengsup; WO2013/56679; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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 55289-36-6 as follows. Computed Properties of C7H8BrN

Reference Production Example 3 (0555) A mixture of 25.0 g of 1-bromo-2-methyl-3-aminobenzene, 60.0 g of triphosgene, and 400 ml of toluene was stirred with heating under reflux for 3 hours. The reaction mixture allowed to cool was concentrated under reduced pressure to obtain 30.3 g of 1-bromo-3-isocyanato-2-methylbenzene. 1-Bromo-3-isocyanato-2-methylbenzene (0556) (0557) 1H-NMR (CDCl3) delta (ppm): 7.39 (1H, dd, 1.5, 7.7 Hz), 7.05 (1H, dd, J=1.7, 8.0 Hz), 7.00 (1H, dt, J=0.5, 8.0 Hz), 2.42 (3H, s).

According to the analysis of related databases, 55289-36-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; HOU, Zengye; TAKAHASHI, Teruki; (156 pag.)US2016/174558; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary