Tag: M.W=200-300

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. 51776-71-7, name is 1-Bromo-4-(difluoromethyl)benzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: bromides-buliding-blocks

Example 38; 4-(4-Difluoromethyl-phenoxy)-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide; A mixture of 4-hydroxy-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide (31a) (102 mg, 0.36 mmol), 1-bromo-4-difluoromethyl benzene (110 mg, 0.53 mmol), Cs2CO3 (174 mg, 0.53 mmol) and CuI (1 mg) in DMF (5 mL) was heated for 2 hr at 160 C. in the microwave. The mixture was filtered and the filtrate was purified by reverse phase chromatograph to give a white solid (18 mg, 12% yield). 1H NMR (400 MHz, CDCl3) delta 9.92 (d, J=2.02 Hz, 1H) 8.52 (s, 1H) 7.72 (dd, J=10.36, 1.77 Hz, 1H) 7.64 (d, J=8.34 Hz, 1H) 7.28 (s, 1H) 7.09 (t, J=7.96 Hz, 1H) 7.05 (s, 1H) 6.97 (s, 1H) 6.77 (d, J=2.02 Hz, 1H) 3.78 (s, 3H) 2.98 (s, 2H) 1.51 (s, 6H); LCMS for C22H21F2N3O3 m/z 414.00 (M+H)+.

The synthetic route of 51776-71-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc.; US2008/280875; (2008); A1;,
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. 86845-28-5, name is 1-Bromo-3-methyl-5-(trifluoromethyl)benzene, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H6BrF3

1-ethenyl-3-methyl-5-(trifluoromethyl)benzene To 1-bromo-3-methyl-5-(trifluoromethyl)benzene (500 mg, 2.51 mmol) was added THF (5 mL), aqueous tribasic potassium phosphate (2.0 M, 4.18 mL, 8.37 mmol), 2-ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (387 mg, 2.51 mmol), palladium(II) acetate (47 mg, 0.209 mmol), and 1,1′-bis(di-t-butylphosphino)ferrocene (99 mg, 0.209 mmol). The system was flushed with nitrogen gas and was heated at 80 C. for 1 hour. The reaction was filtered and then diluted with ethyl acetate and water. The organic layer was dried over sodium sulfate, filtered and concentrated. The crude product was purified by preparative TLC to yield 1-ethenyl-3-methyl-5-(trifluoromethyl)benzene (300 mg, 1.61 mmol). 1H NMR (500 MHz, CDCl3) delta7.47 (s, 1H), 7.40 (s, 1H), 7.34 (s, 1H), 6.76 (m, 1H), 5.85 (d, J=17.6 Hz, 1H), 2.43 (s, 1H).

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; Shao, Pengcheng Patrick; Sun, Wanying; Katipally, Revathi Reddy; Vachal, Petr; Ye, Feng; Liu, Jian; Sha, Deyou; US2013/109649; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 106-37-6, 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. 106-37-6 name is 1,4-Dibromobenzene, 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.

Under nitrogen environment, compound G was dissolved in tetrahydrofuran / toluene (5: 1) and then 0.9 equivalent of compound F was added. After 4.4 equivalent of Potassium carbonate was dissolved in DI water, 0.05 equivalent of Pd (0) was added. The reaction mixture was then refluxed at 80 C. for 24 hours and the reaction was terminated. After extraction with organic solvent, the organic solvent was removed. Compound H was obtained by reprecipitation after a column.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,4-Dibromobenzene, and friends who are interested can also refer to it.

Reference:
Patent; LG Display Co., Ltd.; Yoon Gyeong-jin; Noh Hyo-jin; (33 pag.)KR2019/63923; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 21865-50-9, name is 6-Bromo-2,3,4,9-tetrahydro-1H-carbazole, 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. Computed Properties of C12H12BrN

In a 1 L round-bottom flask, 60.0 g (0.240 mol) of synthesized in [Scheme 2], 73.4 g (0.360 mol) of iobenzene, 2.3 g (0.012 mol) of copper iodide (CuI),Tripotassium phosphate (K3PO4) 106.96 g (0.504 mol),54.8 g (0.480 mol) of trans-1,2-cyclohexanediamineAnd 300.0 ml of 1,4-dioxane was added and refluxed for 12 hours. After the reaction was completed, the mixture was cooled to room temperature, extracted with 1 L of water, and the organic layer was anhydrous and concentrated under reduced pressure. Then, 72.0 g (yield 92.0%) of was obtained by using an adsorption column chromatography.

The synthetic route of 6-Bromo-2,3,4,9-tetrahydro-1H-carbazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SFC Ltd.; Kim Si-in; Kim Nam-i; (52 pag.)KR102017507; (2019); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 139155-55-8, 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. 139155-55-8, name is 1-Bromo-3-isobutylbenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Preparation 15 A mixture of 1-bromo-3-isobutylbenzene (3.16 g), magnesium (1.08 g), 1,2-dibromoethane (2.78 g) and iodine (10 mg) in tetrahydrofuran (10 ml) was refluxed for 1.5 hours. The mixture was cooled to 25 C., and a solution of 3-isobutylbenzaldehyde (2.40 g) in tetrahydrofuran (10 ml) was added at 25 C. After stirred for 1 hour at the same temperature, the mixture was poured into a mixture of ethyl acetate and 1N hydrochloric acid. The organic layer was separated, washed with water and brine, and dried over magnesium sulfate. After evaporation of the solvent, the residue was chromatographed on silica gel (200 g) eluding with 5% ethyl acetate in hexane to give bis(3-isobutylphenyl)methanol (2.90 g) as a colorless oil. NMR (CDCl3, delta): 0.89 (12H, d, J=7.5 Hz), 1.70-1.95 (2H, m), 2.46 (4H, d, J=7.5 Hz), 5.80 (1H, s), 6.97-7.09 (2H, m), 7.09-7.30 (6H, m)

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-3-isobutylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Fujisawa Pharmaceutical Co., Ltd.; US5212320; (1993); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 41825-73-4,Some common heterocyclic compound, 41825-73-4, name is 2-Bromo-4,6-dimethylaniline, molecular formula is C8H10BrN, 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.

Under an argon atmosphere, to a solution of 13.9 g (69.5 mmol) of2-bromo-4,6-dimethylaniline in 200 ml of THF, 27.9 ml of 2.5 M (69.5 mmol) “BuLi in hexanes were added at -5O0C. This mixture was stirred for 2 hours at ambient temperature. The resulting solution was added dropwise over ca. 1 hour, while vigorously stirring, to a solution of 15.0 g (69.5 mmol) of chloro(dimethyl)(2,3,4,5-tetramethyl-2,4-cyclopentadien-l-yl)silane in 100 ml of THF at O0C. The resulting mixture was stirred overnight at ambient temperature, then, evaporated to dryness. To the residue 100 ml of toluene were added. This mixture was filtered through a glass frit (G4). The filtrate was evaporated to dryness. Fractional distillation gave a yellow liquid, bp 180-184C/0.5 mm Hg. Yield 20. I g (77%).Anal. calc. for C19H28BrNSi: C, 60.03; H, 7.46. Found: C, 60.25; H, 7.40.1H NMR (CDCl3): delta 7.15 (s, IH3 3-H in phenyl), 6.82 (s, IH, 5-H in phenyl), 3.10 (br.s, IH, 1-H in Cp), 2.95 (br.s, IH, NH), 2.22 (s, 3H, 4-Me in phenyl), 2.19 (s, 3H, 6-Me in phenyl), 2.01 (s, 6H, 2,5-Me in Cp), 1.83 (s, 6H, 3,4-Me in Cp), 0.15 (s, 6H, SiMe2).13C NMR (CDCl3): delta 140.8, 136.5, 132.7, 131.1, 130.8, 130.7, 130.3, 118.4, 56.3, 20.5, 20.1, 14.5, 11.3, -0.6.

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-4,6-dimethylaniline, its application will become more common.

Reference:
Patent; EXXONMOBIL CHEMICAL PATENTS, INC.; WO2007/70040; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 51776-71-7, A common heterocyclic compound, 51776-71-7, name is 1-Bromo-4-(difluoromethyl)benzene, molecular formula is C7H5BrF2, 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.

In a 10 mL vial charged with [l-[(4,4-difluorocyclohexyl)methyl]-6-(3,5-dimethylisoxazol-4-yl)pyrrolo[3,2-b]pyridin-3- yl]boronic acid (51, 0.05 g, 0.13 mmol) and acetonitrile (4 ml) was added l-bromo-4- (difluoromethyl)benzene (0.05 g, 0.24 mmol), 1M aqueous potassium carbonate (2 ml), and [1, 1′- bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.01 g, 0.01 mmol). The reaction mixture was heated at 140 C in a microwave reactor for 30 min. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and brine. Then, the organic layer was dried over magnesium sulfate and the drying agent removed by filtration. The volatiles were removed from the filtrate under reduced pressure and the crude material was purified by silica gel flash chromatography eluting with 0-50% ethyl acetate in hexane to provide product as a tan solid (P-0608, 18 mg, 28.6%) MS (ESI) [M+H+]+ = 472.0.

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; ZHANG, Jiazhong; BUELL, John; CHAN, Katrina; IBRAHIM, Prabha, N.; LIN, Jack; PHAM, Phuongly; SHI, Songyuan; SPEVAK, Wayne; WU, Guoxian; WU, Jeffrey; WO2014/145051; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 1123172-38-2, name is 1-Bromo-3-(tert-butyl)-5-fluorobenzene, 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 1123172-38-2, category: bromides-buliding-blocks

3-tert-Butyl-5-fluoro-benzaldehyde (Example 21b) To a solution of 1-bromo-3-tert-butyl-5-fluoro-benzene (1.04 g, 4.5 mmol) in anhydrous THF (25 mL) is added under argon a 2.5M solution of nBuLi in hexane (1.9 mL, 4.7 mmol) at -78 C. After stirring for 0.5 h at -78 C. DMF (0.7 mL, 9 mmol) is slowly added by syringe, and the mixture is stirred again for 1.5 h at -78 C. The reaction mixture is added to 0.5N HCl and extracted with Et2O. The product obtained as a light yellow solid is suitable for use in the next step: TLC (hexane-EtOAc 1:1) Rf=0.36; HPLC RtA=2.08 min; 1H-NMR (400 MHz, CDCl3): delta 9.95 (s, 1H), 7.69 (m, 1H), 7.36 (m, 2H), 1.38 (s, 9H). c) 3-tert-Butyl-5-fluoro-benzaldehyde; To a solution of 1-bromo-3-tert-butyl-5-fluoro-benzene (1.04 g, 4.5 mmol) in anhydrous THF is added under Argon at -78 C. 2.5 M nBuLi in hexane (1.9 mL, 4.7 mmol) and after stirring for 0.5 h at -78 C. DMF (0.70 mL, 9 mmol) is added. After stirring for 1.5 h at -78 C. the reaction mixture is added to 0.5 N aqueous HCl and extracted with Et2O. Combined organic layers are washed with brine, dried over MgSO4, filtered and evaporated. The title compound is obtained as a light yellow oil and is used a s such for the next transformation: TLC (hexane-EtOAc 10:1) Rf=0.36; HPLC RtA=2.08 min; 1H-NMR (400 MHz, CDCl3): delta 9.98 (s, 1H), 7.68 (s, 1H), 7.36 (m, 1H), 1.25 (s, 9H).

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; Briard, Emmanuelle; Lueoend, Rainer Martin; Machauer, Rainer; Moebitz, Henrik; Rogel, Olivier; Rondeau, Jean-Michel; Rueeger, Heinrich; Tintelnot-Blomley, Marina; Veenstra, Siem Jacob; US2009/54427; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 41825-73-4, 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 41825-73-4 as follows.

lc N-(2-Bromo-4,6-dimethyl-phenyl)-2-(4-fluoro-phenyl)-acetamide.; 2-Bromo-4,6-dimethyl-aniline (600 mg) and (4-fluoro-phenyl)-acetyl chloride (543 mg) were dissolved in acetonitrile (6 mL) and heated to 150 C for 10 minutes in a sealed microwave process vial. The reaction was cooled to 0 0C, the product filtered off and washed with cold acetonitrile (50 mL) affording 665 mg (66% yield) of the title compound as a white solid. LC-MS (m/z) 337 (MH+); tR = 2.93, (UV, ELSD) 90%, 98%. 1H NMR (500 MHz, DMSOd6): 2.05 (s, 6H), 2.25 (s, 3H), 3.63 (s, 2H), 7.05 (b, IH), 7.15 (dt, 2H), 7.32 (b, IH), 7.40 (dt, 2H), 9.67 (s, IH).

According to the analysis of related databases, 41825-73-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; H. LUNDBECK A/S; WO2006/29623; (2006); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 376646-62-7, 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. 376646-62-7, name is (4-Bromo-2-methylphenyl)methanamine, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of (4-bromo-2-methylphenyl)methanamine (1.2 g, 6 mmol) in DCM (30 mL) were added TEA (1.82 g, 18 mmol) and Boc2O (1.43 g, 6.6 mmol). The mixture was stirred at rt for 1 h. After diluted with water (50 mL), the mixture was extracted with DCM (50 mL x2). The combined organics were washed with brine (50 mL), dried (Na2SO4), filtered and concentrated to give crude title product (1.7 g, yield 95%) as a white solid, which was used directly in the next step without further purification. ESI-MS (M+H): 300.1.

The chemical industry reduces the impact on the environment during synthesis (4-Bromo-2-methylphenyl)methanamine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BIOGEN MA INC.; MACPHEE, J. Michael; HUMORA, Michael; (306 pag.)WO2016/201280; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary