Tag: M.W=200-300

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. 1435-51-4, name is 1,3-Dibromo-5-fluorobenzene, A new synthetic method of this compound is introduced below., Application In Synthesis of 1,3-Dibromo-5-fluorobenzene

General procedure: A solution of m-tolylmagnesium bromide 26, prepared from 416 muL of 3-bromotoluene and 83 mg of magnesium turnings in anhydrous THF (3 mL), was added dropwise under inert atmosphere to a solution of 5-bromovaleronitrile (400 muL, 3.43 mmol) in anhydrous THF (3 mL). The mixture was stirred at room temperature for 1 h, quenched with a saturated aqueous solution of NaHCO3 (3 mL) and extracted with dichloromethane (3 * 10 mL). The combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure. The crude residue was purified by silica gel column chromatography (dichloromethane/methanol 95:5) to provide the compound 7 as a yellow oil (225 mg, 38% yield). Rf = 0.40 (dichloromethane/methanol 95:5). 1H NMR: delta 1.63-1.71 (m, 2H), 1.79-1.87 (m, 2H), 2.37 (s, 3H), 2.60-2.66 (m, 2H), 3.80-3.86 (m, 2H), 7.18-7.29 (m, 2H), 7.51-7.54 (m, 1H), 7.61-7.62 (m, 1H). 13C NMR: delta 20.0, 21.7, 22.1, 27.4, 50.1, 123.3, 126.8, 128.3, 130.5, 138.1, 140.4, 166.2. MS (ESI) m/z [M+H]+ Calcd for C12H16N+: 174.13. Found: 174.2.

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; Matera, Carlo; Quadri, Marta; Sciaccaluga, Miriam; Pome, Diego Yuri; Fasoli, Francesca; De Amici, Marco; Fucile, Sergio; Gotti, Cecilia; Dallanoce, Clelia; Grazioso, Giovanni; European Journal of Medicinal Chemistry; vol. 108; (2016); p. 392 – 405;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 1646-54-4, 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. 1646-54-4 name is 1,4-Dibromo-2,3,5,6-tetramethylbenzene, 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.

To a 3L four necked round bottom flask fitted with refluxedcondenser and mechanical stirrer, were added 1,4-dibromotetramethylbenzene (30 g, 102.73 mmol), pridine(1250 ml) and water (180 ml). The reaction mixture was heated at100 C with constant stirring. To this reaction mixture, KMnO4(82.5 g, 522.15 mmol) was added in small aliquots in 45 min. Aftercomplete addition the reaction mixture was refluxed for next 5 h.The hot solution was filtered to remove MnO2 from reactionmixture and the solvent concentration of at vacuo. To the residualsolid were added water (1500 ml) and NaOH (70 g). The reactionmixture was stirred and heated at 100 C. KMnO4 (82.5 g,522.15 mmol) was added in small aliquots in 1 h. The reactionmixture was refluxed for next 5 h. Excess of KMnO4 was destroyedby caution addition of ethanol (60 ml). The hot solutionwas filteredto separate MnO2. The filtrate was acidified with aqueous HCl (5N).After solvent was removed under reduced pressure, colorlesscompound obtained. Acetonewas added to this solution and stirredfor 40 min. It was filtered to remove NaCl and filtrate wasconcentrated under reduced pressure to obtain 20 g (47%) product.The colorless powder from acetone .13C NMR (Acetone-d6, 75 MHz)deltad 116.41m (CBr), 138.39 (C-COOH), 165.87 (C]O).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,4-Dibromo-2,3,5,6-tetramethylbenzene, and friends who are interested can also refer to it.

Reference:
Article; Bandyopadhyay, Arkasish; Halim, Md. Ershad; Hossain, Md. Elius; Shinmyozu, Teruo; Journal of Molecular Structure; vol. 1213; (2020);,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 2051-99-2, 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. 2051-99-2, name is 1-Bromo-4-isobutylbenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a 50-mL two-neck round-bottom flask equipped with a cannula were added magnesium turnings (608 mg, 25 mmol), and the flask was heated at 80 C in vacuo for 1 h. A solution of the 4-isobutylphenyl bromide (426 mg, 2.0 mmol) in THF (5 mL) was added dropwise over 3 min under argon. The mixture was heated at 50 C until the reaction was initiated. Additional 4-isobutylphenyl bromide (1.71 g, 8.0 mmol) in THF (11.6 mL) was then added slowly via cannula over 15 min. The reaction mixture was heated at reflux for 3 h, after which a solution of 4-isobutylphenyl magnesium bromide 5 was obtained. To a separate 50-mL Schlenk tube was added anhydrous CoBr2 (21.9mg, 0.10mmol), and the tube was heated at 50C in vacuo for 2h. After cooling to room temperature, the cyclopropane-based bisoxazoline ligand 2 (0.12mmol) in THF (3mL) was added under argon. The resulting mixture was stirred for 1h at the same temperature, with 2-bromopropanoate 6 (1mmol) being added via syringe. The mixture solution was cooled to -80C, and the prepared Grignard reagent 5 (2.8mL, 0.5M in THF, 1.4mmol) was then added over 1h via syringe. The reaction mixture was stirred for another 6h at -80C and then quenched with saturated NH4Cl solution (5mL). The aqueous phase was extracted with diethyl ether (4¡Á10mL). The combined organic phases were dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (n-hexane/ethyl acetate 100:1). 4.4.11 (S)-p-Tolyl-2-(4-isobutylphenyl)propanoate 7k Colorless oil, 93% yield, 87:13 er. The enantiomeric ratio was determined by HPLC with a Daicel Chiralcel OJ-H column (15% 2-propanol in n-hexane, 1 mL/min, 220 nm, minor tr = 8.37 min (R), major tr = 13.71 min (S)). [alpha]D20 = +26.4 (c 1.9, CHCl3). 1H NMR (300 MHz, CDCl3) delta 7.31-7.25 (m, 2H), 7.15-7.10 (m, 4H), 6.88-6.85 (m, 2H), 3.92 (q, J = 7.2 Hz, 1H), 2.47 (d, J = 7.2 Hz, 2H), 2.31 (s, 3H), 1.91-1.82 (m, 1H), 1.59 (d, J = 7.2 Hz, 3H), 0.91 (d, J = 6.6 Hz, 6H). 13C NMR (75 MHz, CDCl3) delta 173.4, 148.7, 140.7, 137.4, 135.3, 129.8, 129.5, 127.2, 121.0, 45.3, 45.1, 30.2, 22.4, 20.8, 18.6. HRMS (APCI-TOF): calcd for C20H25O2 [M+H]+ 297.1849, found 297.1842.

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

Reference:
Article; Liu, Feipeng; Bian, Qinghua; Mao, Jianyou; Gao, Zidong; Liu, Dan; Liu, Shikuo; Wang, Xueyang; Wang, Yu; Wang, Min; Zhong, Jiangchun; Tetrahedron Asymmetry; vol. 27; 14-15; (2016); p. 663 – 669;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 176317-02-5, A common heterocyclic compound, 176317-02-5, name is 1-Bromo-2,3,4-trifluorobenzene, molecular formula is C6H2BrF3, 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.

[0510] To a solution of diisopropylamine (10.14 g, 100.20 mmol) in THF (100 mL) was added -BuLi (40.08 mL, 2.5 M in hexane, 100.20 mmol) at -78 C under nitrogen atmosphere. The stirring was maintained at this temperature for 1 h. Then a solution of l-bromo-2,3,4- trifluorobenzene (17.62 g, 83.50 mmol) in THF (120 mL) was added. After stirring for 1 h at -78 C, the mixture was transferred to a bottle with dry ice. The mixture was stirred overnight at room temperature. The reaction was quenched with 10% aqueous HCl and pH was adjusted to 1- 2. The mixture was extracted with ethyl acetate (100 mL x 3). The combined organic extracts were washed with water (100 mL) and brine (100 mL) sequentially, dried over Na2S04, filtered and concentrated under reduced pressure to afford the desired product (20.12 g, 94.5% yield). 1H NMR (400 MHz, DMSO-d6): delta 13.95 (s, 1H), 7.97 (m, 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; TIANJIN BINJIANG PHARMA, INC.; TIAN, Hongqi; JI, Conghui; LIU, Chunlei; KONG, Li; CHENG, Ying; HUANG, Gongchao; WO2013/107283; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 67567-26-4, 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. 67567-26-4, name is 4-Bromo-2,6-difluoroaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Potassium acetate (3.54g, 36.1 mmol) and the boronate (3.36g, 13.2 mmol) were added as solids to a flask then placed under N2. 4-bromo-2,6-difluoroaniline (2.5Og, 12.0mmol) in DMSO (3OmL) was then added to the flask. The reaction was taken through three purge-fill cycles using high vacuum then nitrogen. Pd(dppf)CH2Cl2 (0.129g, 0.159mmol) was added.The reaction was again placed under vacuum then blanketed with nitrogen. The reaction was heated at 80 0C until TLC showed the complete consumption of starting bromide (approximately 90 minutes). The reaction was cooled to room temperature. ETOAc was added, the reaction was then partitioned between EtOAc and saturated aqueous bicarbonate. The organic layer was washed with brine seven times to remove DMSO. The material was then dried with Na2SO4 and concentrated under vacuum. . The residue was chromatographed with eluent 0-100% v/v CEbCVHexanes. Pure product was obtained in 62% yield. 1H-NMR (OMSO-d6) delta 7.03 (dd, J = 6.6Hz, 1.8Hz, 2H), 5.76 (s, 2H) 1.26 (s, 12H); MS [M+H]+ = 256.3, LCMS RT = 3.30 min; R/= 0.37 in 40% CH2Cl2/ Hexanes.

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, 4-Bromo-2,6-difluoroaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2007/64931; (2007); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 22385-77-9,Some common heterocyclic compound, 22385-77-9, name is 1-Bromo-3,5-di-tert-butylbenzene, molecular formula is C14H21Br, 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.

A solution of 1-bromo-3,5-di-tert-butylbenzene (3.380 g, 12.55 mmol, 3 equiv) in THF (25mL) was added dropwise under stirring to magnesium turnings (0.366 g, 15.05 mmol, 3.2equiv), activated with iodine (?0.1 mg). The reaction was stirred for 4 h under reflux, thencooled to ambient temperature and the unreacted Mg was filtered off. The Grignard solutionwas added dropwise to a solution of BiCl3 (1.312 g, 4.16 mmol, 1 equiv) in THF (20 mL) at0 C, and the reaction mixture was stirred overnight at ambient temperature. The solvent wasremoved under vacuum and the green residue was extracted with n-pentane (3 ¡Á 20 mL). After the removal of the solvent, 4 was isolated a colorless solid. Yield: 2.362 g (73percent basedon BiCl3). Single crystals suitable for X-ray analyses were grown from CH2Cl2 solution.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-3,5-di-tert-butylbenzene, its application will become more common.

Reference:
Article; Preda, Ana-Maria; Krasowska, Ma?gorzata; Wrobel, Lydia; Kitschke, Philipp; Andrews, Phil C.; MacLellan, Jonathan G.; Mertens, Lutz; Korb, Marcus; Rueffer, Tobias; Lang, Heinrich; Auer, Alexander A.; Mehring, Michael; Beilstein Journal of Organic Chemistry; vol. 14; (2018); p. 2125 – 2145;,
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. 54962-75-3, name is 3-Bromo-5-(trifluoromethyl)aniline, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 3-Bromo-5-(trifluoromethyl)aniline

3-Bromo-5-(trifluoromethyl)aniline (0.2 mL, 1.43 mmol) was stirred in a solvent of dimethylacetamide (10 mL). The reaction solution was added with 4-methyl-1H-imidazole (0.35 g, 4.26 mmol), K2CO3 (0.20 g, 5.23 mmol), Cu (0.022 g, 0.346 mmol) and CuI (0.068 g, 0.115 mmol), and stirred for about 2 days at 140C. The reaction mixture was diluted with ethyl acetate, and washed with a saturated aqueous sodium bicarbonate solution and saline. The organic layer thus obtained was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain the title compound (0.23 g, 67%). 1H-NMR Spectrum (300 MHz, DMSO-d6): delta 8.06 (s, 1H), 7.36 (s, 1H), 6.96 (s, 1H), 6.92 (s, 1H), 6.80 (s, 1H), 5.86 (s, 2H), 2.14 (s, 3H). MS (ESI+, m/z): 242 [M+H]+

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 54962-75-3.

Reference:
Patent; Hanmi Pharm. Co., Ltd.; BAE, In Hwan; HAN, Sang Mi; KWAK, Eun Joo; AHN, Young Gil; SUH, Kwee Hyun; EP2876107; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 69321-60-4, name is 2,6-Dibromotoluene, 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 69321-60-4, SDS of cas: 69321-60-4

A mixture of 1,3-dibromo-2-methylbenzene (Combi-Blocks catOT-1437: 143 mg, 0.573 mmol), tert-butyl 4-ethynylpiperidine-1-carboxylate (ArkPharm catalog AK-34528: 60 mg, 0.287 mmol), copper(I) iodide (4.37 mg, 0.023 mmol), dichlorobis(triphenylphosphine)-palladium( II) (26.8 mg, 0.038 mmol), and triethylamine (0.080 ml, 0.573 mmol) in 1,4-Dioxane (3.0 ml) was flushed with N2. The resulting slurry was stirred at 90 C. for 3 h. The reaction was then quenched with water, extracted with EtOAc (3¡Á15 mL). The organic layers were combined, dried over Na2SO4, filtered, and the filtrate was concentrated under reduced pressure. The crude residue was purified by chromatography on silica gel, eluting with 0-35% ethyl acetate/hexanes, to give the desired product. LC-MS calculated for C15H17BrNO2 (M+H-tBu)+: m/z=322.0; found 322.0.

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; Incyte Corporation; Wu, Liangxing; Qian, Ding-Quan; Lu, Liang; Lajkiewicz, Neil; Konkol, Leah C.; Li, Zhenwu; Zhang, Fenglei; Li, Jingwei; Wang, Haisheng; Xu, Meizhong; Xiao, Kaijiong; Yao, Wenqing; (101 pag.)US2018/177784; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 5003-71-4, These common heterocyclic compound, 5003-71-4, name is 3-Bromopropan-1-amine hydrobromide, 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.

di-tert-Butyl dicarbonate (3.71 g, 16.9 mmol) and triethylamine (10 mL) were added to a solution of 3-bromopropylamine hydrobromide 7b (3.72 g, 16.9 mmol) in dichloromethane (100 mL). The reaction mixture was stirred at room temperature for 12 h. The progress of the reaction was monitored by TLC. After this time, reaction was complete. The solvent was removed under reduced pressure. A saturated solution of sodium chloride (100 mL) was added to this residue and the mixture was extracted with diethyl ether (2¡Á50 mL). The organic phases were combined, washed with a saturated solution of sodium chloride (3¡Á50 mL) and dried over sodium sulfate. After filtration, the solvent was removed under reduced pressure to give compound 8 in the form of a slightly brown solid. The compound was sufficiently pure to be used in the rest of the synthesis without additional purification (3.50 g, 87%). M.p.: 32-33 C. 1H NMR (200 MHz, CDCl3) delta: 4.63 (s, 1H), 3.42 (t, J=6.5 Hz, 2H), 3.26 (td, J=6.5; 6.5 Hz, 2H), 2.03 (m, J=6.5 Hz, 2H), 1.43 (s, 9H); 13C NMR (125 MHz, CDCl3) delta: 156.09, 79.54, 39.96, 32.82, 30.90, 28.48. HRMS (ESI+) calculated for C8H16NO2Br [M+H]+, m/z 255.0703. found: 255.0695. Rf=0.59 (silica; cyclohexane-ethyl acetate 50:50).

The synthetic route of 5003-71-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CISBIO BIOASSAYS; LAMARQUE, Laurent; PARKER, David; BUTLER, Stephen J.; DELBIANCO, Martina; US2015/361116; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 67567-26-4, These common heterocyclic compound, 67567-26-4, name is 4-Bromo-2,6-difluoroaniline, 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.

A mixture of 4-bromo-2,6-difluoroaniline (2.62 g, 12.6 mmol), methanesulfonyl chloride (1.73 g, 15.1 mmol) and 4-(dimethylamino)pyridine (461 mg, 3.78 mmol) in anhydrous pyridine (35 ml) was stirred for 15 hours at ambient temperature. The mixture was diluted with ethyl acetate (15 ml) and washed with 2M hydochloride aqueous solution until the aqueous pH 2, brine, dried over sodium sulfate. After filtration to separate solvent and sodium sulfate, the solvent was removed under reduced pressure to give a residue, which was applied to a silica gel chromatography column and eluted with hexane/ethyl acetate =5/1 to furnish 2.20 g (48 % yield) of the title compound as a white solid. 1H NMR (DMSO-d6, 270 MHz) delta ppm 3.55 (6H, s), 7.78-7.85 (2H, m)

The synthetic route of 67567-26-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer, Inc.; US2006/100460; (2006); A1;,
Bromide – Wikipedia,
bromide – Wiktionary