Category: bromides-buliding-blocks

Reference of 6698-13-1, A common heterocyclic compound, 6698-13-1, name is 4-Bromo-1,3-benzodioxole, molecular formula is C7H5BrO2, 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.

Tert-butyl piperazine-l-carboxylate (1.11 g, 5.97 mmol) was added to a solution of 4- bromobenzo[d][l,3]dioxole (1 g, 4.97 mmol ) in Toluene (15.0 ml). The resulting suspension was degassed using a stream of argon. Cesium carbonate (2.27 g, 558 mu, 6.96 mmol), racemic- 2,2 -bis(diphenylphosphino)-l, -binaphtyl (232 mg, 373 muiotaetaomicron, Eq: 0.075) and Palladium (II) Acetate (55.8 mg, 249 muiotaetaomicron,) were added to this mixture. The reaction was then heated at 100 C over night. The reaction was cooled to rt, 40ml of water was added and the mixture was extracted with Ethyl Acetate ( 2x 80ml). The organic layers were dried over MgS04 and concentrated under vacuum. The crude material was purified by flash chromatography (silica gel, 50g, 0% to 50% EtOAc in heptane). to yield tert-butyl 4-(benzo[d][l,3]dioxol-4-yl)piperazine-l- carboxylate as a white solid ( 1.15 g, 75%). MS (ISP) m/z = 307.4 [(M+H)+].

The synthetic route of 6698-13-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; RODRIGUEZ SARMIENTO, Rosa Maria; WICHMANN, Juergen; WO2012/110470; (2012); A1;,
Bromide – Wikipedia,
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445-02-3, name is 4-Bromo-2-(trifluoromethyl)aniline, 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. Safety of 4-Bromo-2-(trifluoromethyl)aniline

To a mixture of 2-amino-5-bromobenzotrifluoride (1 .0 g, 4.17 mmol) in DCM (10 mL) at 0-5C was added NEt3 (1 .16 mL, 8.33 mmol), then methanesulfonyl chloride (0.389 mL, 5 mmol) dropwise. The reaction mixture was stirred at rt for 4 days. After 2 days, more NEt3 was added (1 .16 mL, 8.33 mmol). As there was no evolution after 3 days, more NEt3 (0.580 mL, 4.17 mmol) and methanesulfonyl chloride (0.324 mL, 4.17 mmol) were added. The reaction was not completed, so the reaction mixture was then heated in a microwave oven at 1 10C for 20 min. There was no evolution, so the reaction was stopped. The reaction mixture was diluted with water and DCM. Layers were separated. The organic layer was washed with water, dried over MgS04 and evaporated. Purification by Flash chromatography using CombiFlash Companion ISCO system (Redisep silica 40g column, eluting with Cyclohexane/EtOAc 100:0 to 70:30) did not give the pure compound. Purification by prep HPLC using Gilson system (SunFire C18 column, eluting with H20 + 0.1 % TFA / CH3CN 20% to 85%) gave the title compound (404 mg, 31 % yield) as a white solid. 1 H-NMR (400 MHz, DMSO-d6, 298 K): ? ppm 3.12 (s, 3H) 7.55 (d, 1 H) 7.91 (d, 1 H) 7.92 (s, 1 H) 9.56 (s, 1 H). MS(10): 316.3-318.2 [M-1 ]

The synthetic route of 445-02-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; FURET, Pascal; HEBACH, Christina; HOeGENAUER, Klemens; HOLLINGWORTH, Gregory; LEWIS, Ian; SMITH, Alexander, Baxter; SOLDERMANN, Nicolas; STAUFFER, Frederic; WOLF, Romain; ZECRI, Frederic; WO2013/57711; (2013); A1;,
Bromide – Wikipedia,
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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. 615-36-1, name is 2-Bromoaniline, A new synthetic method of this compound is introduced below., Computed Properties of C6H6BrN

General procedure: The 25 mL RB flask was charged with arylboronic acid (1 mmol), N-nucleophile (2 mmol), Ni(OAc)2*4H2O/1a (10 mol % of Ni(II) salt and 20 mol % of 1a), TMG (2 mmol), and toluene (1 ml). The reaction mixture was stirred at 60 C for 24 h. After completion of the reaction, the reaction mixture was cooled to room temperature, diluted with ethyl acetate (20 mL), and washed with brine water. The combined organic phase was dried over anhydrous Na2SO4. After removal of the solvent, the residue was subjected to column chromatography on silica gel using hexane to afford the Chan-Lam product in high purity.

The synthetic route of 615-36-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Keesara, Srinivas; Tetrahedron Letters; vol. 56; 48; (2015); p. 6685 – 6688;,
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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. 112734-22-2, name is (4-Bromo-2-fluorophenyl)methanamine, A new synthetic method of this compound is introduced below., name: (4-Bromo-2-fluorophenyl)methanamine

Step 1: (4-Bromo-2-fluorophenyl)methanamine (924 mg, 4.53 mmol) was dissolved in pyridine and ethane sulfonyl chloride (0.82 mL, 8.60 mmol) was added to the solution at 0 C. The mixture was stirred for 1 h at 0 C. Then, the mixture was quenched with 1N HCl and extracted with ethyl acetate. Drying over magnesium sulfate and evaporation of the ethyl acetate and purified by column chromatography gave N-(4-bromo-2-fluorobenzyl)-ethanesulfonamide in pure form (1.06 g, 79%).

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; Gruenenthal GmbH; FRANK, Robert; Bahrenberg, Gregor; Christoph, Thomas; Lesch, Bernhard; Lee, Jeewoo; US2013/79320; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 13633-25-5, These common heterocyclic compound, 13633-25-5, name is 1-Bromo-4-phenylbutane, 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 ethyl-2-(diethoxyphosphoryl) acetate 5 in DMF(25 mL/mol) was stirred at 0 C. The base was added and the solutionwas continued to stir for 20 min before the alkyl halide wasadded drop wise. The reaction mixture was allowed to warm toroom temperature and then heated at 60 C for 18 h. After coolingthe reaction mixture was acidified with 10% citric acid andextracted with diethyl ether (3 x 30 mL). The combined organicphases were washed with H2O (3 x 30 mL), brine (1 30 mL) anddried over Na2SO4. The product 6a-c was purified with columnchromatography using 2:1 diethyl ether/pentane as eluent.

Statistics shows that 1-Bromo-4-phenylbutane is playing an increasingly important role. we look forward to future research findings about 13633-25-5.

Reference:
Article; Skagseth, Susann; Akhter, Sundus; Paulsen, Marianne H.; Muhammad, Zeeshan; Lauksund, Silje; Samuelsen, Ørjan; Leiros, Hanna-Kirsti S.; Bayer, Annette; European Journal of Medicinal Chemistry; vol. 135; (2017); p. 159 – 173;,
Bromide – Wikipedia,
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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 2789-89-1 as follows. COA of Formula: C14H8Br2

General procedure: The photocatalyst [Ir(dF-CF3-ppy)2(dtbpy)]PF6 (PC-1) (11.2 mg, 0.01 mmol, 2.0 mol%) wasadded to an oven-dried Schlenk tube containing a magnetic stirring bar and anhydrous ethylacetate (2.5 mL, 0.2 M) was added under argon. In the absence of light, the enone (0.5 mmol,1.0 equiv) and the alkyne (1.0 mmol, 2.0 equiv) were added under an argon stream. Theresulting solution was degassed using three freeze-pump-thaw cycles and the tube was finallybackfilled with argon. The reaction mixture was allowed to stir at room temperature for 24 hunder irradiation with visible light from two 30 W Kessil LEDs (lambdamax = 455 nm, see chapter 1.2).The solvent was evaporated and the crude reaction products were purified by columnchromatography over silica gel (dry load of crude material, pentane/EtOAc or pentane/diethylether mixtures as eluent) to afford products 6a-6e, 9a-9e and 10.

According to the analysis of related databases, 2789-89-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Strieth-Kalthoff; Henkel, Christian; Teders, Michael; Kahnt, Axel; Knolle, Wolfgang; Gomez-Suarez, Adrian; Dirian, Konstantin; Alex, Wiebke; Bergander; Daniliuc, Constantin G.; Abel; Guldi, Dirk M.; Glorius; Chem; vol. 5; 8; (2019); p. 2183 – 2194;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 18392-81-9,Some common heterocyclic compound, 18392-81-9, name is 5,6-Dibromobenzo[c][1,2,5]thiadiazole, molecular formula is C6H2Br2N2S, 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 mixture of N,N?-1,3-bis(2,6-diisopropylphenyl)imidazolium chloride [51] (0.45 g, 1.06 mmol) and Pd(OAc)2 (0.13 g, 0.59 mmol) in toluene (4mL), a suspension of NaOt-Bu (0.16g, 1.66mmol) in dry toluene (3mL) was added under inert conditions. The solution was heated at 88C for 30min. This mixture was cooled to room temperature and added to a pressure tube containing 2 [41] (2.00g, 6.8mmol) in toluene (70mL). To this mixture, tert-butylamine (1.5mL, 14.27mmol) was added followed by NaO-tBu (1.60g, 16.65mmol). The pressure tube was sealed and heated for 16hat 130C. After cooling, the reaction mixture was filtered through Celite. The filtrate was collected and evaporated to yield 3 as a light brown solid (1.941g, crude yield). The crude product was engaged in the following reaction with no further purification. 1H NMR (CDCl3, 300MHz): delta 7.14 (s, 2H, ArH), 3.40 (br, 2H, NH), 1.41 (s, 18H, CH3).

The synthetic route of 18392-81-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tapu, Daniela; Buckner, Ossie J.; Boudreaux, Chance M.; Norvell, Bradley; Vasiliu, Monica; Dixon, David A.; McMillen, Colin D.; Journal of Organometallic Chemistry; vol. 823; (2016); p. 40 – 49;,
Bromide – Wikipedia,
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Synthetic Route of 105309-59-9, 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. 105309-59-9 name is Tetrakis(4-bromophenyl)methane, 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.

Cz (2.5 g, 8.9 mmol), intermediate TBrBen (2.8 g, 4.5 mmol), CuI (0.19 g, 1.0 mmol) and K3PO4 (1.69 g, 8.0 mmol) were added to 100 mL of toluene.The reaction was carried out under argon gas protection and reflux for 24 hours.After removing the solvent, the residue was extracted with dichloromethane (3×100 mL).The organic phases were combined and dried over anhydrous magnesium sulfate.The residue obtained by concentration was purified by column chromatography using dichloromethane: n-hexane (7:3) as eluent to afford product DCzCBr (2.7 g, yield 50.3%).Identification of intermediates by mass spectrometry,The result is:

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Tetrakis(4-bromophenyl)methane, and friends who are interested can also refer to it.

Reference:
Patent; Yangtze Normal University; Yang Yezi; Yao Chuang; Sun Changqing; (13 pag.)CN108752320; (2018); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 586-61-8, The chemical industry reduces the impact on the environment during synthesis 586-61-8, name is 1-Bromo-4-isopropylbenzene, I believe this compound will play a more active role in future production and life.

[0001248] A mixture of l-bromo-4-isopropylbenzene (30 mg, 0.15 mmol), Compound 356A (75 mg, 0.15 mmol), [l, -bis(diphenylphosphino)ferrocene]dichloropalladium(II) (7 mg, 8.2 muiotaetaomicron), sodium carbonate (32 mg, 0.30 mmol), water (0.5 mL), and 1,4-dioxane (5 mL) was stirred under nitrogen atmosphere at 80 C for 2 h. After cooling, the reaction mixture was treated with water (5 mL), extracted with ethyl acetate (10 mL x 3), washed with brine (5 mL), dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified with prep-HPLC to furnish Compound 357. LC-MS (ESI) m/z: 547 [M+H]+; 1H- NMR ((CD3)2CO, 400 MHz): delta (ppm) 1.64 (m, 6H), 2.08-2.11 (m, 3H), 2.17-2.23 (m, 1H), 2.96-3.043 (m, 4H), 3.17-3.82 (m, 4H), 4.21-4.33 (m, 3H), 4.37 (d, 1H), 4.69-5.75 (m, 2H), 6.85-7.07 (m, 2H), 7.35-7.43 (m, 2H), 7.46-7.79 (m, 3H), 7.81-7.87 (m, 1H), 7.89-7.98 (m, 1H), 8.02-8.14 (m, 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-4-isopropylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BIOMARIN PHARMACEUTICAL INC.; WANG, Bing; CHU, Daniel; BRIDGES, Alexander, James; WO2015/42397; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 65896-11-9, name is 2-Bromo-6-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. name: 2-Bromo-6-fluoroaniline

At 15 deg.C, 2-bromo-6-fluoroaniline (1.00 g, 5.26 mmol) and dimethylphosphine oxide (451.84 mg, 5.79 mmol) in water (20ml) mixture was added potassium carbonate ( 2.91 g, 21.05 mmol) and Pd / C (150 mg). The reaction mixture was stirred at 160 deg.C microwave heating for 3 hours. TLC (petroleum ether: ethyl acetate = 10: 1) showed the reaction was complete. The reaction mixture (20mL × 4) and extracted with dichloromethane. The combined organic layer was filtered, the filtrate was concentrated and purified by column chromatography (dichloromethane: methanol = 1: 0-10: 1) afforded the title compound (100mg, yield 10.16%) 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 65896-11-9, its application will become more common.

Reference:
Patent; Nanjing Mingde New Drug Research and Development Co. Ltd.; Qilu Pharmaceutical Co., Ltd.; Ding, Zhaozhong; Zhang, Minghui; Chen, Shuhui; Liu, Xile; Zhu, Yidong; Fan, Chuanwen; Zhao, Baoping; Zhang, Long; Chen, Dong; Yang, Yingying; Zheng, Qingmei; Zheng, Shansong; Wan, Haiwen; Hu, Jinqing; (93 pag.)CN105330698; (2016); A;,
Bromide – Wikipedia,
bromide – Wiktionary