Month: January 2021

Related Products of 1422-54-4,Some common heterocyclic compound, 1422-54-4, name is 2-Bromo-6-fluorotoluene, molecular formula is C7H6BrF, 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.

1-Bromo-3-fluoro-2-methylbenzene (388 mg, 2.05 mmol), and (4-methoxyphenyl)methanol (0.511 mL, 4 mmol) were dissolved in DMF (5 mL) in a microwave vessel. Sodium hydride as a 60% dispersion in mineral oil (164 mg, 4.0 mmol) was added portionwise under a flow of nitrogen over 10 min. The reaction vessel was then sealed and heated at 180 C. for 900s. The crude reaction mixture was poured onto 1:1 water:brine (6 mL) and DCM (10 mL). The biphasic mixture was stirred at ambient temperature for 1 h and then the organic and aqueous layers were separated. The combined organics were dried over Na2SO4 and concentrated in vacuo. The crude material was then purified by chromatography on silica gel. Elution with 5:95 ethyl acetate:heptane afforded 1-bromo-3-(4-methoxybenzyloxy)-2-methylbenzene (289 mg, 0.9 mmol, 46%).

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-6-fluorotoluene, its application will become more common.

Reference:
Patent; N.V. Organon; US2007/185156; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 327-52-6, name is 1-Bromo-2,4,5-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. Product Details of 327-52-6

This example illustrates step 2 of the process of the invention: Heck coupling of 1-bromo-2,4,5-trifluorobenzene with 1-benzyl-4-methyl-2-methylenesuccinate with selective formation of (E)-1-benzyl-4-methyl-2-(2,4,5-trifluorobenzylidene)succinate, compound (IV). [Show Image] A 1000 mL round bottomed flask fitted with magnetic stirrer, thermometer, nitrogen inlet and reflux condenser is charged with 1-benzyl-4-methyl-2-methylenesuccinate (100.0 g, 0.43 mol), 1-bromo-2,4,5-trifluorobenzene (124.0 g, 0.59 mol), methyl dicyclohexyl amine (127.0 g, 0.65 mol), dimethyl acetamide (215 mL), water (53 mL) and lithium bromide (7.5 g, 0.09 mol). The mixture is degassed with three vacuum-nitrogen cycles; palladium acetate (260 mg, 1.16 10-3 mol) is then added as reaction catalyst. The mixture is heated with stirring at 95-98 C for 22 hours monitoring by GC until > 95% conversion, then cooled to room temperature, added of water (500 mL) and toluene (250 mL) and filtered on a Celite pad. The organic phase is washed with 1N HCl (200 mL), dried by azeotropic distillation under reduced pressure, treated with coarse silica gel (20 g), filtered and concentrated to a residue (128 g). Gas-chromatographic analysis of the crude product shows the following composition: 87% (E)-1-benzyl-4-methyl-2-(2,4,5-trifluorobenzylidene)succinate, 7% (Z)-1-benzyl-4-methyl-2-(2,4,5-trifluorobenzylidene)succinate, 4% (E)- and (Z)-1-benzyl-4-methyl 2-(2,4,5-trifluorobenzyl)maleate, 2% starting material. An analytical sample of pure (E)-1-benzyl-4-methyl-2-(2,4,5-trifluorobenzylidene)succinate is obtained by flash chromatography with gradient elution 0?20% AcOEt in hexane. 1H NMR (300 MHz, CDCl3) delta 7.77 (s, 1H), 7.40-7.34 (m, 5H), 7.22 (ddd, J=15.3, 8.6, 6.7 Hz, 1 H), 6.97 (ddd, J=15.9, 15.9, 6.4 Hz, 1 H), 5.26 (s, 2H), 3.66 (s, 3H), 3.43 (s, 2H).

The synthetic route of 1-Bromo-2,4,5-trifluorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chemo Iberica, S.A.; EP2423178; (2012); 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

Adding a certain compound to certain chemical reactions, such as: 2270-59-9, name is 5-Bromo-2-methylpent-2-ene, 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 2270-59-9, Safety of 5-Bromo-2-methylpent-2-ene

Potassium carbonate (49 mg), potassium iodide (29.4 mg) and 5-bromo-2-methyl- 2-pentene (35.3 muL) was added to a solution of Compound No. 12 (62 mg) in acetonitrile (3 mL). The mixture was stirred at 800C for 5 hours and subsequently at room temperature overnight. The mixture was concentrated under reduced pressure and the residue thus obtained was partitioned between dichloromethane and water. The separated organic layer was washed with water and brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure. The residue thus obtained was purified by preparative column chromatography to yield the title compound. Yield: 27mg1H NMR (CDCl3):delta 7.43-7.33 (1OH, m), 5.07-5.04 (IH, m), 3.65-3.47 (IH, m), 3.15-2.05 (13H, m), 21.78-1.73 (6H, m), 1.33-1.1 (4H, m).Mass (m/z): 433 (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, 5-Bromo-2-methylpent-2-ene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; RANBAXY LABORATORIES LIMITED; WO2007/39884; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 4333-56-6,Some common heterocyclic compound, 4333-56-6, name is Bromocyclopropane, molecular formula is C3H5Br, 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 5-bromo-2-chlorophenol (543 mg, 2.62 mmol), bromocyclopropane (836 mul, 10.47 mmol) and caesium carbonate (1.701 g, 5.24 mmol) in N,N-dimethylacetamide (7.5 ml) was stirred for 47 h at 150 C. After 25.25 h further bromocyclopropane (836 mul, 10.47 mmol) was added. The reaction mixture was poured onto ice-water (40 ml) and set to pH=2 with aqueous HCl (1 N, 9.5 ml). This mixture was extracted with TBME (twice 50 ml). The organic layers were washed with brine (40 ml), combined and dried over sodium sulfate. Concentration and purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 67:33) afforded the title compound (570 mg, 87%) as a light yellow oil. MS m/e: 248.0 [M+H]+

The synthetic route of 4333-56-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Knust, Henner; Nettekoven, Matthias; Pinard, Emmanuel; Roche, Olivier; Rogers-Evans, Mark; US2009/312314; (2009); 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. 72678-19-4, name is 2,6-Dibromo-4-(trifluoromethyl)aniline, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H4Br2F3N

A mixture of 2,6-dibromo-4-trifluoromethylaniline (manufactured by Wako Pure Chemicals, 0.78 g, 2.45 mmol) and 95% sulfuric acid (1.5 mL) was cooled to an internal temperature of 0 C., and 40% nitrosylsulfuric acid (0.85 g, 2.67 mmol) was dropwise added thereto at the internal temperature kept at 0 C. This was stirred for 1 hour at an internal temperature of from -2 C. to 0 C., and with cooling with ice, this was poured into 5 mL of ice in water to give a diazo liquid. In a separate vessel, the intermediate A-1 (1.00 g, 2.67 mmol) was dissolved in acetic acid (2 mL), and dropwise added to the resultant diazo liquid at an internal temperature of 0 C. or lower. After the addition, this was left at 0 C. for 1 hour, then extracted with toluene, and the toluene layer was washed with water and saturated saline water, and dried with anhydrous sodium sulfate. This was concentrated under reduced pressure, and purified through silica gel column chromatography to give an intermediate C-1 (0.33 g, yield 19%) as a reddish tar-like substance.

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; MITSUBISHI CHEMICAL CORPORATION; SHIGA, Yasushi; AOBA, Mitsuya; TANAKA, Yuki; ISHIDA, Mio; US2015/191601; (2015); 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

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. 348-57-2, name is 1-Bromo-2,4-difluorobenzene, A new synthetic method of this compound is introduced below., Application In Synthesis of 1-Bromo-2,4-difluorobenzene

To a solution of compound 97-4 (10 g, 51 mmol) in anhydrous THF (100 mL) was added slowly LDA (25 mL, 62 mmol) at ?78¡ã C., and the reaction solution was stirred for 1 h, after which ethylchlorosilane (10.5 mL, 57 mmol) was added and the resulting solution was stirred ?78¡ã C. for 2 h. After TLC indicated the reaction was complete, the reaction was quenched with saturated NH4Cl solution (aq., 100 mL), and the aqueous phase was extracted with EtOAc (200 mL¡Á3). The organic phases were combined, dried over anhydrous Na2SO4, filtered and evaporated to dryness by rotatory evaporation to give compound 97-5 (15.7 g, Yield 100percent, colourless oily liquid) which was directly used for the next step. LCMS (ESI) m/z: 309 (M+1) 1H NMR (CDCl3, 400 MHz): delta ppm 7.53-7.47 (m, 1H), 6.74 (t, J=8.4 Hz, 1H), 0.98-0.82 (m, 15H)

The synthetic route of 348-57-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hubei Bio-Pharmaceutical Industrial Technological Institute Inc.; Humanwell Healthcare (Group) Co., Ltd.; Wang, Xuehai; Wu, Chengde; Xu, Yong; Shen, Chunli; Li, Li’e; Hu, Guoping; Yue, Yang; Li, Jian; Guo, Diliang; Shi, Nengyang; Huang, Lu; Chen, Shuhui; Tu, Ronghua; Yang, Zhongwen; Zhang, Xuwen; Xiao, Qiang; Tian, Hua; Yu, Yanping; Chen, Hailiang; Sun, Wenjie; He, Zhenyu; Shen, Jie; Yang, Jing; Tang, Jing; Zhou, Wen; Yu, Jing; Zhang, Yi; Liu, Quan; (251 pag.)US2017/313683; (2017); 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

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