Tag: M.W=100-200

Some common heterocyclic compound, 5433-01-2, name is 1-Bromo-3-isopropylbenzene, molecular formula is C9H11Br, 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 5433-01-2

1 -Bromo-3-isopropylbenzene (200 g, 954 mmol, 1 eq) is dissolved in 1 I of 1-methyl-2-pyrro- lidone. Zinc cyanide (114 g, 954 mmol, 1 eq) and Pd(PPh3)4 (28.7 g, 24.8 mmol, 0.03 eq) are added under nitrogen. The reaction mixture is heated to 125C, stirred at this temperature for 150 min, then cooled to rt and filtered over Hyflo Super Gel, and the filtrate is diluted with H2O and EtOAc. The organic layer is washed with water, 1 N HCI solution and brine, dried -~ over sodium sulfate, filtered and concentrated. The residue is purified by column chromatography using DCM/hexane in a ratio of 1 to 3 to give the product. HPLC (Nucleosil C18HD, 4×70 mm, 3 mum, 20-100% MeCN (6 min), 100% MeCN (3 min)) retention time: 5.06 min.1H-NMR (400 MHz, CDCI3): 7.57 (s, 1H), 7.53-7.48 (m, 2H), 7.43 (t, 1H), 3.01-2.92 (m, 1H), 1.29 (d, 6H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5433-01-2, its application will become more common.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2007/77004; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 103-64-0,Some common heterocyclic compound, 103-64-0, name is (2-Bromovinyl)benzene, molecular formula is C8H7Br, 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.

Example 35; [0145] 1 ,3-Bis(2,4,6-trimethylylphenyl)-4-phenyl- 1H- 1 ,2,3-triazoliumhexafiuorophosphate (lOba), alternate preparation. To a stirred suspension of triazene 8b (5.63 g, 20 mmol) and anhydrous potassium hexafiuorophosphate (3.68 g, 10 mmol) and beta- bromostyrene 11a (mixture of isomers, 5.13 mL, 40 mmol) in dry dichloromethane (100 mL) in the dark at -78C is added tert-butyl hypochlorite (3.33 mL, 30 mmol), upon which the mixture instantly darkens. The mixture is stirred overnight as it is slowly allowed to warm to room temperature. The contents are then filtered, and the solid residue is washed with dichloromethane. The filtrate is collected, and volatiles are evaporated under reduced pressure. Diethyl ether is then added, and the mixture is vigorously triturated for ca. Ihour, with occasional scratching of the glass surfaces to ensure efficient mixing. Filtration and washing with copious quantities of diethyl ether afford, after drying under vacuum, triazolium salt lOba as an off-white solid (10.21 g, 97%). Analytical samples were obtained after recrystallization by vapor diffusion of diethyl ether in an acetonitrile solution of lOba. Characterization data are identical as for lOba prepared by the first method.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (2-Bromovinyl)benzene, its application will become more common.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; BERTRAND, Guy; GUISADO-BARRIOS, Gregorio; BOUFFARD, Jean; DONNADIEU, Bruno; WO2011/139704; (2011); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 4333-56-6, name is Bromocyclopropane, 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 4333-56-6, Quality Control of Bromocyclopropane

A 5 L flask fitted with a magnetic stirrer was charged with Mg turnings (106 g, 4.34 mol, 1.58 equiv) and anhydrous THF (2.00 L) and purged with N2. Mg was activated by addition of Br2 (1 mL, 19.5 mmol) and stirring at rt for 15 min. A solution of cyclopropyl bromide (500 g, 4.13 mol, 1.5 equiv) in anhydrous THF (1.9 L) was added slowly over 2 h. The reaction was kept on ice during the addition and the rate controlled so the internal temperature was kept below 35 C. After addition the mixture was stirred at rt for 1.5 h then cooled on ice overnight. The next day the reaction was gently warmed to 22 C to redissolve most of the precipitate and used in the following step.

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; CHEMOCENTRYX, INC.; FAN, Junfa; KALISIAK, Jaroslaw; LUI, Rebecca, M.; MALI, Venkat, Reddy; MCMAHON, Jeffrey, P.; POWERS, Jay, P.; TANAKA, Hiroko; ZENG, Yibin; ZHANG, Penglie; (194 pag.)WO2016/187393; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 766-46-1, name is 2′-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 766-46-1, Safety of 2′-Bromophenylacetylene

General procedure: A THF solution (5.0 mL) of 1 (1.0 mmol) was treated with Bu3SnOMe (1.0 mmol) and t-BuOK (0.5 mmol). The mixture was stirred for 4.5 h under nitrogen at reflux. The reaction mixture was then treated with 3 (207.1 mg, 0.98 mmol), P(t-Bu)3 (0.035 mmol) and Pd2(dba)3 (0.018 mmol) at room temperature, and the mixture was stirred under nitrogen at room temperature for 8 h. After workup with diethylether (3 × 10.0 mL)/NH4Faq (10%, 10.0 mL), the organic layer was dried over MgSO4. After filtration, the solvents were evaporated. The crude product was subjected to column chromatography on silica gel to afford 4a-i. 4a,13 4b,10 4c,14 4d,14 4e,14 4f,14 4g,15 4h14 and 4i14 are known compounds and were identified by their previously reported spectroscopic data.

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, 2′-Bromophenylacetylene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Peng, Li-Fen; Wang, Bing-Hao; Wang, Ming; Tang, Zi-Long; Jiang, Yan-Zi; Jiao, Yin-Chun; Xu, Xin-Hua; Journal of Chemical Research; vol. 42; 5; (2018); p. 235 – 238;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 21120-91-2, 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 21120-91-2 as follows.

In a 250 ml three necked round bottom flask equipped with a polytetraflouroethylene (Teflon polymer, Dupont, Wilmington, Del.) coated magnetic stir bar, potassium hydroxide (1.38 g, 1 eq) was dissolved in water (6.83 g). Then 4-acetoxy styrene (4 g, 1 eq) was added dropwise at room temperature, and the solution turned from colorless to pale orange. Potassium carbonate (6.82 g, 2 eq) was added portionwise, and the solution was stirred for one hour. The flask was equipped with a reflux condenser, then 1-bromobenzocyclobutene (4.06 g, 1 eq) was added dropwise in DMF (41 ml). The solution was then heated to 70 C. and allowed to reflux overnight. To the reaction was added water (50 ml) and ethyl acetate (50 ml). The aqueous residue was extracted four times with ethyl acetate (100 ml). The combined organics were extracted with sodium bicarbonate solution (1×100 ml), lithium chloride aqueous solution (1×100 ml) and brine (2×100 ml). The organics were dried over sodium sulfate, filtered and concentrated in vacuo to give the product as a of white solid (3.36 g, 68% yield). Melting point 54-60 C. 1H NMR (600 MHz, Chloroform-d) delta 7.39 (d, J=8.6 Hz, 2H), 7.34 (td, J=7.3, 1.5 Hiz, 1H), 7.31-7.24 (m, 2H), 7.21-7.18 (m, 1H), 6.98 (d, J=8.6 Hz, 2H), 6.69 (dd, J=17.6, 10.9 Hz, 1H), 5.70 (dd, J=4.3, 1.9 Hz, 1H), 5.64 (dd, J=17.6, 0.9 Hz, 1H), 5.15 (dd, J=10.9, 0.9 Hz, 1H), 3.73 (dd, J=14.2, 4.3 Hz, 1H), 3.31 (d, J=14.2 Hz, 1H). 13C NMR (151 MHz, Chloroform-d) delta 157.79, 144.62, 142.57, 136.20, 130.87, 129.93, 127.50, 127.43, 123.48, 123.04, 115.06, 111.80, 74.28, 39.45. Yield from the above example was good and the resulting monomer was a stable solid which has a desirable ring opening cure temperature of 184 C.

According to the analysis of related databases, 21120-91-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Rohm and Haas Electronic Materials LLC; Hayes, Colin; Gallagher, Michael K.; Riener, Michelle; (10 pag.)US2019/169327; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 766-81-4, These common heterocyclic compound, 766-81-4, name is 3-Bromophenylacetylene, 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.

Step d); Preparation of Compound 6; A mixture of 5 (0.450 g, 0.88 mmol) and 4 M HCl/dioxane (2.25 mL) in dioxane (7 mL) was stirred at room temperature for 3 h then heated to 50 C. for 1 h. After this time additional 4 M HCl/dioxane (2.25 mL) and dioxane (10 mL) were added and the mixture was stirred at room temperature for an additional 17 h. The reaction mixture was then concentrated to half the original volume then diluted with ether (50 mL). The resulting precipitate was filtered and washed with ether to afford 6 (0.164 g, 56%) as a yellow solid: 1H NMR (400 MHz, CDCl3) delta 8.11 (s, 1H), 7.89 (s, 1H), 7.72 (s, 1H), 7.60 (s, 1H), 7.47 (s, 2H), 4.38-4.36 (m, 2H), 2.83 (dd, J=14.2, 7.0 Hz, 2H), 1.38-1.33 (m, 3H), 1.21-1.15 (m, 3H).

Statistics shows that 3-Bromophenylacetylene is playing an increasingly important role. we look forward to future research findings about 766-81-4.

Reference:
Patent; Wyeth; US2007/4786; (2007); 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. 10485-09-3, name is 2-Bromoindene, A new synthetic method of this compound is introduced below., Quality Control of 2-Bromoindene

The synthesis of the naphthyl ligand is shown in scheme 2. 2-bromoindene (6.66 g, 0.0342 moles) was taken in a round-bottomed flask and dissolved in toluene. Tetrakis triphenyl phosphine palladium (0.054gm, 8mol%) was added to the above solution and stirred for 10-15 min. To this solution the diboronic acid from step 1 (3g, 0.0156 moles) dissolved in ethanol (5ml) was added, followed by aqueous sodium carbonate (2M, 10ml). The reaction mixture was heated to 80C and stirred for 24hrs. It was cooled and extracted with dichloromethane (DCM; 5 x 50ml). The DCM portion was then extracted with water (2 x 50ml), dried over sodium sulfate and concentrated. The crude compound was purified by column chromatography by continuously eluting with hexane as the eluent. Crude yield = 3g; Purified yield = 1.6g (33%)

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; SAUDI BASIC INDUSTRIES CORPORATION; SABIC GLOBAL TECHNOLOGIES B.V.; SANKARAN, Nedumbamana; SHINGE, Prashant Sukumar; SHETTY, Sharankumar; CHANDRA, Girish; AL-SHAMMARI, Haif; AL-HUMYDI, Abdulaziz Hamad; NESAKUMAR, Edward Joseph; NADKARNI, Pradeep Jeeevaji; WO2015/28595; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 586-61-8, 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. 586-61-8 name is 1-Bromo-4-isopropylbenzene, 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.

Example 1This example illustrates the preparation of Compound E1 , 3-iso- propyl-N6,N6,N12,N12-tetrakis(3,4-dimethylphenyl)-chrysene-6,12-diamine a. Preparation of (Z)-1 -(4-/so-propylstyryl)naphthalene.In a drybox, 1-vinylnaphthalene (9.80 g, 63.5 mmol) and 4- bromocumene (11.5 g, 57.8 mmol) were placed into a 250 ml RB flask and dissolved in 80 ml of dry DMF. Palladium catalyst (frans-di(mu- acetato)bis[o-(di-o-tolylphosphino)benzyl] dipalladium (II), 0.542 g, 0.58 mmol) and sodium acetate (7.11 g, 86.6 mmol) were added last, followed by 20 ml of dry DMF. The flask was capped, taken out of the box and attached to a condenser flushed with nitrogen. The reaction mixture was stirred at 120 0C for 60 hours. Solution was cooled to room temperature and poured into 750 ml of water. Aqueous layer was extracted with CH2Cb (3×500 ml). Combined organic layers were rinsed with water and brine (500 ml each), dried over MgSO4 and volatiles were removed under vacuum. Crude product was adsorbed onto 25 g of silica, loaded onto a 4″ column and eluted with hexane first, then with 20% CH2CI2 in hexane. The first fraction was concentrated and residue was dried under high vacuum to 6.3 g (40 %) of the desired product. 1H NMR is analogous to the one reported in the literature (Beckmann et al., Solid St. Nuc. Mag. Res., 1998, 12, 251 ).

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

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; WO2008/147721; (2008); 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. 10269-01-9, name is (3-Bromophenyl)methanamine, This compound has unique chemical properties. The synthetic route is as follows., Formula: C7H8BrN

General procedure: Appropriate amine (1.5 equiv) was added to a solution ofcompound 19 or 20 in EtOH (5 mL) at room temperature.The mixture was stirred at room temperature for 2 h to 3 dand evaporated. The residue was purified by a flash silicagel column chromatography (CH2Cl2:MeOH = 20:1) togive compounds 1-8.

According to the analysis of related databases, 10269-01-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Yu, Jinha; Kim, Gyudong; Jarhad, Dnyandev B.; Lee, Hyuk Woo; Lee, Jiyoun; Park, Chong Woo; Ha, Hunjoo; Jeong, Lak Shin; Archives of Pharmacal Research; vol. 42; 9; (2019); p. 773 – 779;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 38573-88-5, 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. 38573-88-5 name is 1-Bromo-2,3-difluorobenzene, 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.

General procedure: In a 15 mL sealed tube equipped with a magnetic stirring bar were added 1 (1 mmol),2 (0.8 mmol), tert-butyl isocyanide (1.2 mmol, 136 muL), Pd(OAc)2 (0.03 mmol, 7 mg),DPEPhos (0.06 mmol, 32 mg), Cs2CO3 (0.8 mmol, 261 mg), and anhydrous DMF (2.0mL). The tube was purged with argon, and the contents were stirred at 100 °C for 2 h.Then Na2S*9H2O (1.2 mmol, 240 mg) was added for 2 h. After reaction completion,the mixture was filtered through a pad of Celite, and DMF was removed by a vacuum.The combined filtrates were refluxed in THF (15 mL) and oxalic acid (1 M, 3 mL) for 8h. The solvents were removed under reduced pressure, then poured into brine (20mL) and extracted by ethyl acetate (3 × 30 mL). The combined organic layers weredried (Na2SO4) and evaporated. The residue was purified on a silica gel column usingpetroleum ether/ethyl acetate as the eluent to give the pure target product.

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

Reference:
Article; Zhang, Fang-Ling; Chen, Zhen-Bang; Liu, Kui; Yuan, Qing; Jiang, Qing; Zhu, Yong-Ming; Synlett; vol. 29; 5; (2018); p. 621 – 626;,
Bromide – Wikipedia,
bromide – Wiktionary