Month: July 2021

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. 6274-57-3, name is 1-(4-Bromophenyl)-N,N-dimethylmethanamine, A new synthetic method of this compound is introduced below., HPLC of Formula: C9H12BrN

General procedure: To a stirred solution of 10 (1.00g, 4.00mmol) and K2CO3 (1.66g, 12.00mmol) in acetonitrile (20mL) was added dropwise diethylamine solution (1.20g, 16.00mmol) at room temperature for 2h. The solvent was evaporated in vacuo and the residue was then dissolved in EtOAc (50mL) and washed with water (20mL×3), the organic layers were washed with brine, and dried over anhydrous Na2SO4. The solvent was evaporated under reduced pressure to provide the 11a (0.83g, 84.7% yield) as an off-white liquid. (0041) Then, a mixture of 11a (0.83g, 3.43mmol), bis(pinacolato)diboron (0.96g, 3.77mmol), PdCl2(dppf)-CH2Cl2 (0.084g, 0.103mmol) and potassium acetate (0.67g, 6.86mmol) in anhydrous 1,4-dioxane (15mL) was purged with argon and heated at 100C for 2.5h. The reaction was then treated with 6 (1.20g, 3.60mmol), 2.0M aqueous Na2CO3 (5mL) and another portion of PdCl2(dppf)-CH2Cl2 (0.084g, 0.103mmol), then heated at 110C for 12h under argon. The reaction mixture was cooled to room temperature, filtered, and concentrated. The final compound was purified by MPLC (ISCO CombiFlash purification system) (MeOH/DCM, eluted from 0% to 10%), The fractions were collected, concentrated to afford 12a (0.72g, 57.2% yield).

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; Han, Jinsong; Chen, Ying; Yang, Chao; Liu, Ting; Wang, Mingping; Xu, Haojie; Zhang, Ling; Zheng, Canhui; Song, Yunlong; Zhu, Ju; European Journal of Medicinal Chemistry; vol. 122; (2016); p. 684 – 701;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 1073-06-9, name is 1-Bromo-3-fluorobenzene, 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. Recommanded Product: 1-Bromo-3-fluorobenzene

Charge an oven-dried 250 mL round-bottom flask with 6-methoxy-1-tetralone (3. 0g, 17.0 mmol. ) and place under nitrogen. Dissolve the solid in toluene (30mL) and add 1-bromo-3-fluorobenzene (4. 7 mL, 42.6 mmol), sodium t-butoxide (6.5g, 68.1 mmol), palladium acetate (76mg, 0.34 mmol), and racemic BINAP (212mg, 0.34 mmol). Heat the solution to 115C and stir for 18 hours. Dilute the solution with cold 5N HC1 (50mL) and ethyl acetate (200mL). Separate the organic layer and dry over sodium sulfate, filter over a pad of celite and concentrate in vacuo. Purify the crude product using radial chromatography to give 3.4 g (74%) of the title compound. This material is used without further purification: mass spectrum (ion spray) m/z =267 (M-H). Dissolve 2- (3-fluoro-phenyl)-6-methoxy-naphthalen-l-ol (3.36g, 12.5 mmol) in N-methyl-2-pyrrolidinone (NMP) (lOmL) and add sodium hydride (500mg, 60% oil dispersion, 12.5 mmol) at room temperature. After stirring for 1 hour this solution is added to a solution of 4-fluorobenzaldehyde (2.4mL, 22.5 mmol) in NMP (lOmL) that has been heated to 185C. Continue stirring for 2.5 hours. Cool the reaction to room temperature and add pH 7 buffer (50mL) and extract with ethyl acetate (2 X 100mL). Wash the organic extracts with water and filter through a plug of silica gel. Purify the crude product using radial chromatography giving 2. 50g (54%) of the title compound and use without further purification: mass spectrum (ion spray) m/z = 371 (M-H). Charge a 100 mL round-bottom flask with 4- [2- (3-fluoro-phenyl)-6-methoxy- naphthalen-l-yloxy]-benzaldehyde (2. 5g, 6.71 mmol) and ethyl acetate (5 mL). At room temperature add 2 mL of 35% hydrogen peroxide. To this solution slowly add 2 mL of concentrated sulfuric acid. The mixture warms to approximately 40 C and returns to room temperature where it is stirred for 2 hours. Dilute the reaction with water and ethyl acetate (100 mL) and dry the organic layer over sodium sulfate, filter and concentrate in vacuo. Purify the crude product using radial chromatography eluting with CH2C12 to yield 540 mg (22%) of the title compound: mass spectrum (ion spray) m/z = 359 (M-H).

The synthetic route of 1-Bromo-3-fluorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/73204; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 61613-22-7,Some common heterocyclic compound, 61613-22-7, name is 2-Bromo-N-phenylaniline, molecular formula is C12H10BrN, 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.

10 g (42 mmol) of 2-bromo-N-phenylaniline and 150 ml of tetrahydrofuran were added to a reaction container, and the mixture was cooled to -78?C using dry ice. After 3.323 g (52 mmol) of n-butyllithium was slowly dropwise added thereto, the resulting solution was stirred for 1 hour. 17.6 g (52 mmol) of bis(4-bromophenyl)methanone was dissolved in 50 ml of tetrahydrofuran, and slowly dropwise added to the reaction container. After the reaction was completed, the solvent was evaporated and the resulting residue was thoroughly dried. 100 ml of acetic acid:hydrochloric acid (1:10 volume by volume (v/v)) was added thereto, thereby obtaining 15.2 g (yield: 77%) of Intermediate I-4-1.

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-N-phenylaniline, its application will become more common.

Reference:
Patent; Samsung Electronics Co., Ltd.; Samsung SDI Co., Ltd.; JEON, Soonok; KIM, Sangmo; KIM, Hyungjun; CHUNG, Yeonsook; JUNG, Yongsik; CHAE, Miyoung; HUH, Dalho; KIM, Joonghyuk; IHN, Sooghang; (87 pag.)US2017/5275; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

28148-04-1, name is 1,3-Dibromo-2-methylpropane, 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: C4H8Br2

General procedure: Kinetic parameters were determined using a halide release assay. Assays were done at room temperature in 200 muL 50 mM Tris-SO4, pH 8.2. For compound 1e, 20% of DMSO was added to enhance the solubility to 0.5 mM. Samples were taken at different times and after adding mercuric thiocyanate and ferric ammonium sulfate the absorption was measured at 460 nm. [27] and [53] The initial rates of halide release at different substrate concentrations were plotted in a Michaelis-Menten graph in order to determine the kinetic parameters.Time-course experiments were done as follows. To 10 mL of a solution of compound 1 in 50 mM Tris-SO4, pH 8.2, enzyme was added and the mixture was incubated at 30 C (for details, see Table 5). At various times, 1 mL samples were taken and extracted with a solvent containing dodecane as internal standard. The samples were dried with MgSO4. The enantiomeric excess values for haloalcohols 2a-2c were determined by Chiral GC and for 2d and 2c by chiral HPLC, as described above. For the reactions with compounds 1a, 1b and 1c, the conversion was determined with the same GC program, whereas for 1d and 1e a different GC program was used. For 1d: AT5 GC column (80 C?130 C (10 C/min), 130 C for 1 min, 130 C?80 C (20 C/min), retention times 3.8 min (2d) and 4.4 min (1d)). For 1e: AT5 GC column (80 C?180 C (10 C/min), 180 C for 1 min, 180 C?80 C (20 C/min), retention times: 10.9 min (2e); 11.9 min (1e)).

The synthetic route of 28148-04-1 has been constantly updated, and we look forward to future research findings.

Reference:
Conference Paper; Westerbeek, Alja; Van Leeuwen, Jan G.E.; Szyma?ski, Wiktor; Feringa, Ben L.; Janssen, Dick B.; Tetrahedron; vol. 68; 37; (2012); p. 7645 – 7650;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 766-81-4, name is 3-Bromophenylacetylene, 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 766-81-4, category: bromides-buliding-blocks

The 3′-bromophenylacetylene (181 mg, 1.0 mmol), cat. [Au] (6 mg, 1 muM %), AgOTf (2.6 mg, 1 muM %), water (36 mg, 2 mmol) and methanol (1 ml) are added to the 25 mL of Claisen tube or. After closing the reaction at 120 C for 6 hours, cooling to room temperature. Then adding formic acid amine (315 mg, 5 mmol) and cat. [Rh] (6.2 mg, 1 mmol %), the reaction mixture in oil bath heated to 80 C, reaction 12 hours, cooling to room temperature. Rotary evaporation of the solvent and add a certain amount of ethyl acetate and water extraction, the organic phase of the resulting product after concentrated hydrochloric acid the reflux process, rotary evaporation to remove the solvent, the final petroleum ether washing and filtering to obtain the pure target compound, yield: 83%

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; Nanjing University of Science and Technology; Li Shun; Xu Meng; Li Feng; (12 pag.)CN109384677; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 2695-48-9, 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. 2695-48-9, name is 8-Bromo-1-octene, This compound has unique chemical properties. The synthetic route is as follows.

A 250-mL round-bottom flask equipped with a stir bar and a water-jacketed reflux condenser was charged with trimethylsilylacetylene (6.00 mL, 42.0 mmol). THF (50 mL) was added, and the mixture was allowed to cool to 0 C (ice-bath). nButyllithium (29.0 mL, 42.0 mmol, 1.46 M solution in hexanes) was added dropwise by a syringe, and the ice-bath was removed following the addition. The mixture was allowed to warm to 22 C as it stirred for 1 h, at which point 8-bromo- l-octene (3.50 mL, 21.0 mmol) was added, and the mixture was allowed to reflux for 12 h. The mixture was allowed to cool to 0 C, quenched by addition of 50 mL water, washed with CH2CI2 (5 x 50 mL). The combined organic layers were washed in brine ( 1 x 50 mL), dried over MgS0 , filtered, and concentrated in vacuo. The resulting brown oil was filtered through a plug of silica gel (eluted in pentane), the filtrate was concentrated and the resulting brown oil distilled under vacuum ( 1.0 torr). The resulting yellow oil was re-distilled under vacuum ( 1.0 torr) to afford dec-9-en- l -ynyltrimethylsilane (0.700 g, 3.40 mmol, 14.0% yield) as a colorless oil. IR (neat): 3078 (w), 2929 (m), 2857 (w), 2175 (m), 1641 (w), 1461 (w), 1325 (w), 1248 (m), 1032 (w), 994 (w), 910 (m), 837 (s), 758 (s), 725 (w), 697 (w), 638 (m), 575 (w), 450 (w); NMR (400 MHz, CDCb): delta 5.86-5.76 ( 1 H, m), 4.99 ( 1 H, dd, J= 17.2, 2.0 Hz), 4.93 ( 1 H, dd, J= 10.0,0.8 Hz), 2.21 (2H, t, J= 7.2 Hz), 2.05 (2H, app q, J= 7.1 Hz), 1.55- 1.48 (2H, m), 1.40- 1.28 (6H, m), 0. 14 (9H, s); , 3C NMR ( 100 MHz, CDCI 3 ) : delta 1 39.2, 1 14.4, 107.8, 84.4, 33.9, 28.9, 28.8, 28.7, 28.7, 20.0, 0.3 ; HRMS (EST) [M+HJ+ calcd for C^H^Si: 209.1726, found: 209.1719.

The chemical industry reduces the impact on the environment during synthesis 8-Bromo-1-octene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; TRUSTEES OF BOSTON COLLEGE; MASSACHUSETTS INSTITUTE OF TECHNOLOGY; HOVEYDA, Amir, H.; MEEK, Simon, J.; O’ BRIEN, Robert, V.; CROS, Josep, Llaveria; SCHROCK, Richard, R.; WO2011/97642; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 766-81-4, 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. 766-81-4, name is 3-Bromophenylacetylene, This compound has unique chemical properties. The synthetic route is as follows.

In 25 ml in the reactor, adding O-bromophenyl (0.034 g, 0.2 mmol) and cuprous iodide (0.004 g, 0 . 02 mmol) butyl potassium (0.045 g, 0.4 mmol), vacuum replace the nitrogen after three times by adding 3 – bromophenylacetic acetylene (0.054 g, 0.3 mmol) and water (0.015 g, 0.8 mmol), in anhydrous 1, 4 – dioxane 1.5 ml, 110 C under stirring 16 h after. Column chromatography (silica gel, 200 – 300 mesh; developing agent, petroleum ether: ethyl acetate=5:1) to obtain 3 – (3 – bromophenylacetic methylene) isoindoline -1 – one 0.042 g, yield 70%.

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

Reference:
Patent; Dalian University of Technology; Bao Ming; Li Pengcheng; Zhang Sheng; Wang Wanhui; (24 pag.)CN109912492; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 4117-09-3, 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. 4117-09-3, name is 7-Bromo-1-heptene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 1 Synthesis of Nonenoic Acid (Compound 19) Sodium ethoxide was added to a solution of diethylmalonate in ethanol. To this solution was added 1-bromo-hept-6-ene. The reaction mixture was concentrated and then treated with aqueous potassium hydroxide. The reaction mixture was acidified and then heated at 140 C. to ensure decarboxylation and give nonenoic acid (19).

The synthetic route of 7-Bromo-1-heptene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Achillion Pharmaceuticals Inc.; Phadke, Avinash; Hashimoto, Akihiro; US9006423; (2015); B2;,
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. 553-94-6, name is 2,5-Dimethylbromobenzene, A new synthetic method of this compound is introduced below., name: 2,5-Dimethylbromobenzene

Under argon atmosphere, arylbromides (0.6 mmol), palladium catalyst (0.5 mol%), KOtBu(0.6 mmol) and DMF (5 mL) were added to a schlenck containing a magnetic stir bar, followedby (0.6 mmol) of phenylacetylene. The resulting mixture was placed in an oil bath preheatedto 100 C and stirred vigorously for the indicated time. Upon completion, the mixture wascooled to room temperature, was partitioned between 30 mL of water and 20 mL of diethyletheror ethyl acetate and the combined organic layer was further washed with 2 × 20 mLof diethylether or ethyl acetate and was dried over MgSO4. The extraction was done withDCM when 2,6-dibromopyridine was used as a substrate. The ltrate was sampled at intervalsfor GC analysis to check the purity and the conversions are based on arylbromides.

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; Boubakri; Mansour; Harrath; Oezdemir; Ya?ar; Hamdi; Journal of Coordination Chemistry; vol. 71; 2; (2018); p. 183 – 199;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 52723-82-7, name is 4-Bromo-5-fluoro-2-methylaniline, 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 52723-82-7, HPLC of Formula: C7H7BrFN

Acetic anhydride (1.488 mL, 15.77 mmol) was added to a suspension of 4-bromo-5- fluoro-2-methylaniline (1.6087 g, 7.88 mmol) in chloroform (18 mL) under ice-bath cooling and the mixture stirred at RT for 5 min. Potassium acetate (0.812 g, 8.28 mmol), a solution of 18-crown-6 (0.417 g, 1.577 mmol) In chloroform (4 mL) and then t-butyl nitrite (2.186 mL, 16.56 mmol) were then added and the mixture heated at 75°C for 16 h. The dark brown mixture was then cooled, DC (20 mL) added and the organic layer washed with saturated aqueous sodium bicarbonate solution (ca. 20 mL) then reduced. The residue was purified by chromatography on silica gel eluting with a gradient of 0-30percent ethyl acetate in hexane. Impure fractions were purified further by chromatography on silica gel eluting with a gradient of 0-20percent ethyl acetate in isohexane. All pure fractions were combined and then reduced to afford the title compound as a light orange solid (984 mg). 1H N R (CDCl3l 400MHz) delta ppm: 2.79 (3H, s), 7.95 (1 H, dd, 6.5 Hz, 0.5 Hz), 8.07 (1H, d, J 1.0 Hz), 8.25 (1 H, dd, J 9.0, 0.5 Hz).

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; GLAXO GROUP LIMITED; BAILEY, James; KING, Nigel Paul; LIN, Xichen; REN, Feng; TAN, Kheng-Chuan; MAK, Sing Yeung; WO2011/72488; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary