Month: March 2021

142808-15-9, name is 4-Bromo-2-fluorobenzotrifluoride, 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: 4-Bromo-2-fluorobenzotrifluoride

step 2: To a solution of 4-bromo-2-fluoro-l-(trifluoromethyl)benzene (4.854 g, 19.98 mmol) and ether (50 mL) cooled to -78 C was added butyl lithium (7.990 mL, 19.98 mmol) slowly over 10 min. The reaction was transferred via cannula to a solution of 74 (4.30 g, 16.65 mmol) in THF (50 mL) cooled to -78 C. The reaction was stirred for 10 min after all aryl lithium was added. The reaction was quenched with water and extracted with DCM. The organic layer was concentrated and the crude product purified by Si02 chromatography eluting with an EtOAc/hexane (1 to 5% EtOAc). A close running impurity was not removed by this purification. A Si02 column was run eluting with an Et20/hexane gradient (1 to 3% Et20). The impurity was still present and the compound was finally purified on a SP4 reverse phase column chromatography eluting with MeCN/water gradient (65 to 100% MeCN) to afford 2.105 g (33.2%) of (R)-tert-butyl 2-(3-fluoro-4-(trifluoromethyl)benzoyl)-pyrrolidine-l-carboxylate (76).

The synthetic route of 142808-15-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARRAY BIOPHARMA INC.; GENENTECH, INC.; BLAKE, James F.; CHEN, Huifen; CHICARELLI, Mark Joseph; DEMEESE, Jason; GARREY, Rustam; GAUDINO, John J.; KAUS, Robert J.; KOLAKOWSKI, Gabrielle R.; MARLOW, Allison L.; MOHR, Peter J.; REN, Li; SCHWARZ, Jacob; SIEDEM, Christopher S.; THOMAS, Allen A.; WALLACE, Eli; WENGLOWSKY, Steven Mark; WO2012/118850; (2012); A1;,
Bromide – Wikipedia,
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Synthetic Route of 4117-09-3, These common heterocyclic compound, 4117-09-3, name is 7-Bromo-1-heptene, 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.

Grignard reagent hept-6-en-1-ylmagnesium bromide was prepared by suspending magnesium granules (0.22g, 9.05mmol) in anhydrous tetrahydrofuran (20mL) and subsequently adding 7-bromo-1-heptene (1.63g, 9.19mmol) dropwise. The mixture was refluxed for 30min. In a separate flask, copper(I) iodide (1.72g, 9.03mmol) was suspended in anhydrous tetrahydrofuran (10mL) and cooled to-78C in an isopropyl alcohol-dry ice bath. Methyllithium solution (1.6M in diethyl ether, 5.65mL, 9.04mmol) was added very slowly via syringe. The resultant mixture was stirred at-78C for 1h and then slowly allowed to warm to 0C, whereupon a brownish suspension formed, which was immediately cooled to-78C. After that, the aforementioned solution of Grignard reagent in tetrahydrofuran was added via syringe. The mixture thus obtained was stirred at-78C for 1h and then allowed to warm to 0C, whereupon a purple colouration appeared. The mixture was then cooled again to-78C and a solution of 1 (1.47g, 4.51mmol) in tetrahydrofuran (20mL) was added via syringe. That mixture was allowed to stir at-78C for 1h and at room temperature for 2h, and the reaction was quenched by adding saturated aqueous ammonium chloride (15mL). After addition of diethyl ether (50mL), two layers and a brown insoluble formed which was filtered off. The organic phase was separated and the royal blue aqueous phase was extracted with diethyl ether. The combined organic fractions were washed with brine, dried over anhydrous magnesium sulphate, filtered and concentrated under reduced pressure. Flash column chromatography of the residual brown oil with n-hexane-diethyl ether (95:5) yielded the crude ester mixture (0.56g, 42%). A 0.23g portion was separated from the by-product 3 by passing over a 10g SPE cartridge. Step gradient elution from acetonitrile-water (9:1) to pure acetonitrile yielded pure ester 2 as a white solid (0.20g, 96%) after concentration under reduced pressure. TLC (n-hexane-diethyl ether 9:1): Rf 0.43. RP-TLC (acetonitrile): Rf 0.22. 1H NMR (400MHz, CDCl3): delta 5.80 (1H, ddt, J=16.9, 10.1, 6.6Hz), 5.00-4.89 (2H, m), 3.65 (3H, s), 2.28 (2H, t, J=7.4Hz), 2.05-1.99 (2H, m), 1.60 (2H, qui, J=7.3Hz), 1.38-1.20 (24H, m). 13C NMR (100MHz, CDCl3): delta 174.4, 139.3, 114.1, 51.5, 34.2, 33.9, 29.7 (3), 29.6, 29.5, 29.3, 29.2, 29.0, 25.0. GC: tR 16.6min. EIMS (70eV): m/z (%) 296 (1), 264 (51), 222 (28), 180 (19), 111 (19), 97 (45), 87 (59), 74 (83), 55 (100), 41 (58).

The synthetic route of 4117-09-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Huber, Thimo; Firlbeck, Doris; Riepl, Herbert M.; Journal of Organometallic Chemistry; vol. 744; (2013); p. 144 – 148;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 1647-26-3, name is 1-Bromo-2-cyclohexylethane, molecular formula is C8H15Br, 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

Preparation 3 1-(2-Cyclohexylethyl)-1H-imidazole-4-carboxaldehyde Imidazole-4-carboxaldehyde (4.8 g, 50 mmol) was added portionwise to a suspension of sodium hydride (2.20 g, 60% dispersion in mineral oil, 55 mmol) in tetrahydrofuran (150 ml), and the mixture was then stirred at room temperature for 1 hour. 2-Cyclohexylethyl bromide (8.6 ml, 55 mmol) was added, and the mixture was heated under reflux for 18 hours. The cooled mixture was evaporated under reduced pressure and the residue was partitioned between water (500 ml) and dichloromethane (500 ml). The layers were separated, and the organic phase was dried (MgSO4) and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel using an elution gradient of toluene:ethyl acetate (100:0 to 96:4) to afford the title compound, 1.78 g. 1H-NMR (CDCl3, 400 MHz) delta: 0.98 (m, 2H), 1.20 (m, 4H), 1.68 (m, 7H), 4.00 (t, 2H), 7.4 (s, 1H), 7.60 (s, 1H), 9.80 (s, 1H). LRMS: m/z (TSP+) 207.2 [MH+].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1647-26-3, its application will become more common.

Reference:
Patent; Pfizer Inc.; US2003/199522; (2003); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 138526-69-9, These common heterocyclic compound, 138526-69-9, name is 1-Bromo-3,4,5-trifluorobenzene, 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.

Argon gas protection 1000ml three-necked bottle, add cyclobutene benzoic acid 60g,77 g of 3,4,5-trifluorobromobenzene was added, and 5 g of tetrabutylammonium bromide was added.188 g of absolute ethanol was added, stirred until fully dissolved, and the temperature was raised to 40 C, and 0.6 g of a palladium chloride catalyst was added.Continue to heat up to 68 ~ 72 C weak reflux,Temperature control 68 ~ 72 C drop added Sodium carbonate 100g / water 200g solution,After the dropwise addition, the reaction was kept at this temperature for 4 h, the reaction was stopped, 200 g of toluene was added, and 200 g of water was added.Stir for 2h, separate the liquid, wash to neutral, dry, filter, and concentrate to obtain the product.GC analysis content >95%, yield >98%.

The synthetic route of 138526-69-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shandong Shenghua Science And Technology Chuangyeyuan Co., Ltd.; Wu Shengxi; Liu Yuyang; Wang Dexian; Du Kaichang; Gao Genhua; (10 pag.)CN108178720; (2018); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 766-81-4, A common heterocyclic compound, 766-81-4, name is 3-Bromophenylacetylene, molecular formula is C8H5Br, 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: In a glove box filled with nitrogen, to an oven-dried 5 mL pressure tube equipped with a stir bar were added CuI (0.015 mmol, 2.9 mg, 0.050 equiv), 4,4′-di-tert-butyl-2,2′-dipyridine (2.0 mg, 0.0075 mmol, 0.025 equiv), azide compounds (0.36 mmol, 1.2 equiv), terminal alkynes (0.30 mmol, 1.0 equiv), (CF3CF2CO)2O (0.39 mmol, 120.9 mg, 1.3 equiv), Et3N (0.45 mmol, 45.5 mg, 1.5 equiv) and THF/n-C6H14 (1:1, 1.0 mL). The tube was sealed with Teflon screw cap and the solution was stirred at 50 C for 15 h. The reaction mixture was cooled to room temperature and was filtered through a layer of Celite, eluted with dichloromethane. The solvent was removed by rotary evaporation and the resulting product was purified by column chromatography on silica gel with n-pentane/ dichloromethane.

The synthetic route of 766-81-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lin, Bo; Wu, Wei; Weng, Zhiqiang; Tetrahedron; vol. 75; 19; (2019); p. 2843 – 2847;,
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. 51554-93-9, name is 1-Bromo-4-octylbenzene, A new synthetic method of this compound is introduced below., name: 1-Bromo-4-octylbenzene

General procedure: A 3-neck round-bottomed flask equipped with a thermometer and a condenser was flame-dried and flushed with Ar. The flask was then charged with Mg0 (1.1 eq.), a single I2 crystal and another vacuum/Ar cycle was performed. Et2O (C=0.65M) was added resulting in a bright orange suspension of Mg0 pellets. Phenyl octyl bromide (1.0 eq.) was then added in one portion and the suspension was heated via a heatgun until the internal temperature reached 32C and stabilized for 5-10s, indicating that the Grignard formation had started. The reaction was stirred at rt until disappearance of the starting material by 1H NMR analysis (e.g.?1h). (0031) The Grignard solution (3.0 eq., C=0.65M) was then syringed to another flask containing substrate (1.0. eq.) in dry Et2O (C=0.05M). The solution was stirred at rt until disappearance of the starting material by TLC analysis. Saturated aqueous NH4Cl solution was added and the aqueous layer was extracted x2 with EtOAc. The organic layers were collected, washed x1 brine, dried over Na2SO4, filtered, concentrated in vacuo.

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; Garsi, Jean-Baptiste; Sernissi, Lorenzo; Vece, Vito; Hanessian, Stephen; McCracken, Alison N.; Simitian, Grigor; Edinger, Aimee L.; European Journal of Medicinal Chemistry; vol. 159; (2018); p. 217 – 242;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 69321-60-4, 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. 69321-60-4 name is 2,6-Dibromotoluene, 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.

According to scheme 2, step viii: To a mixture of intermediate 15b (2 g, 5.68 mmol,1 eq) and 1,3-dibromo-2-methylbenzene (1.42 g, 5.68 mmol, 72.57 uL, 1 eq) in dioxane (30 mL) and H2O (2 mL) were added Pd(dppf)Cl2 (207.76 mg, 283.93 umol, 0.05 eq) and Na2CO3 (1.81 g, 17.04 mmol, 3 eq) in one portion at 25C under N2. The mixture was stirred at 90C for 12 hours. The residue was poured into ice-water (w/w = 1/1) (50 mL). The aqueous phase was extracted with ethyl acetate (50 mL x 3). The combined organic phase was washed with brine (50 mL), dried with anhydrous Na2SO4, filtered and concentrated in vacuo to afford Intermediate 53 (1.4 g, 3.54 mmol, 62.37% yield) as a yellow solid. 1H NMR (CDCl3, 400 MHz) delta 8.92 (d, J = 4.8 Hz, 2H), 7.75 (s, 1 H), 7.54 (d, J = 7.6 Hz, 1 H), 7.40 (t, J = 4.8 Hz, 1 H), 7.11-7.06 (m, 2H), 6.24 (s, 1 H), 3.00 (t, J = 9.6 Hz, 2H), 2.64 (t, J = 9.6 Hz, 2H), 2.42 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,6-Dibromotoluene, and friends who are interested can also refer to it.

Reference:
Patent; Pragma Therapeutics; DUVEY, Guillaume; CELANIRE, Sylvain; (118 pag.)EP3459939; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 845866-81-1,Some common heterocyclic compound, 845866-81-1, name is 2-Bromo-1-(difluoromethyl)-4-fluorobenzene, molecular formula is C7H4BrF3, 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 2-difluoromethyl-5-fluorobenzaldehyde used as starting material was prepared as follows :-; Isopropylmagnesium chloride – lithium chloride complex (IM, 21.46 mL, 21.46 mmol) was added to 2-bromo-l-(difluoromethyl)-4-fluorobenzene (4.39 g, 19.51 mmol) in THF (120 mL) cooled to -200C under nitrogen. The resulting solution was stirred at -200C for 1 hour. N,N-Dimethylformamide (1.813 mL, 23.41 mmol) was added, and the mixture stirred for a further 1 hour, maintaining the temperature in the range -15 to -200C. The mixture was allowed to warm to ambient temperature, then 2M hydrochloric acid (100 mL) was added and the mixture was extracted with EtOAc (150 mL). The organic layer was washed with saturated sodium bicarbonate (120 mL) and concentrated to yield crude product. The crude product was purified by flash silica chromatography, elution gradient 5 to 10% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford 2- (difluoromethyl)-5-fluorobenzaldehyde (1.250 g, 36.8%) as a colourless liquid. IH NMR (399.9 MHz, CDC13) delta 7.26 (IH, t), 7.37 – 7.43 (IH, m), 7.63 – 7.67 (IH, m), 7.78 – 7.82 (IH, m), 10.19 (IH, d); m/z = 173 [M-H]-.

The synthetic route of 845866-81-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BRADBURY, Robert, Hugh; CARR, Gregory, Richard; RABOW, Alfred, Arthur; RAO KORUPOJU, Srinivasa; TUMMA, Harikrishna; WO2010/92371; (2010); A1;,
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. 103-64-0, name is (2-Bromovinyl)benzene, This compound has unique chemical properties. The synthetic route is as follows., category: bromides-buliding-blocks

At room temperature,To the appropriate amount of the organic solvent DMF was added 100 mmol of the compound of the above formula (I)220 mmol of the compound of formula (II)6 mmol of catalyst (2.4 mmol of Pd (TFA) 2 with 3.6 mmol of Cu (acac) 2)50 mmol of 1-ethyl ethyl ether-3-methylimidazolebis (trifluoromethanesulfonyl) imide and 300 mmol of triisopropanolamine,Then heated to 80 C,And the reaction was stirred at that temperature for 6 hours; After the reaction,The resulting mixture was filtered while hot,To obtain a filtrate;To the filtrate was added a 10% hydrochloric acid solution with a mass percentage of 10%Adjust the pH to neutral;Then ethyl acetate,Oscillation extraction 2-3 times,Combined organic phase,Dried over anhydrous magnesium sulfate,Then concentrated under reduced pressure,The resulting residue was subjected to 200-300 mesh silica gel column chromatography,The petroleum ether-n-butanol mixture was used as the eluent,Wherein the volume ratio of petroleum ether to n-butanol is 10: 1,Thereby obtaining a compound of the above formula (III)The yield was 97.4%.

According to the analysis of related databases, 103-64-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Qingdao University; Xia Yunqiu; Zhou Yingbin; Wang Yanxin; Zhong Weizhen; Guo Shenbo; (9 pag.)CN104803912; (2017); B;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 10269-01-9, name is (3-Bromophenyl)methanamine, 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 10269-01-9, Quality Control of (3-Bromophenyl)methanamine

A mixture of (3-bromophenyl)methanamine (5.4 g, 29 mmol), AcCl (2.7 g, 29 mmol) and Et3N (5.9 g, 58 mmol) in DCM (100 mL) was stirred at rt for 3 h, then it was quenched with water (20 mL) and extracted with DCM (3 x 20 mL). The combined organic layers were concentrated in vacuo. The residue was recrystallized from hexanes/EtOAc (10/1, 55 mL) to afford the title compound. 1H NMR (CDC13, 400 MHz): delta 7.40-7.36 (m, 2H), 7.20- 7.15 (m, 2H), 6.01 (br s, 1H), 4.37 (d, / = 6.0 Hz, 2H), 2.01 (s, 3H).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; CHILDERS, Matthew Lloyd; DINSMORE, Christopher; FULLER, Peter; GUERIN, David; KATZ, Jason David; PU, Qinglin; SCOTT, Mark E.; THOMPSON, Christopher F.; ZHANG, Hongjun; FALCONE, Danielle; TORRES, Luis; BRUBAKER, Jason; ZENG, Hongbo; CAI, Jiaqiang; DU, Xiaoxing; WANG, Chonggang; BAI, Yunfeng; KONG, Norman; LIU, Yumei; ZHENG, Zhixiang; WO2014/146490; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary