Category: 766-81-4

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 766-81-4 as follows. Safety of 3-Bromophenylacetylene

In a 25 mL roundbottom flask, 1-bromo-3-ethynylbenzene (243 muL, 1.94 mmol, 1.1 equiv) was dissolved in 10 mL THF and cooled to-78 C. A solution of LiHMDS (1 M in THF, 1.9 mL, 1.85 mmol, 1.05 equiv) was added dropwise, then the mixture allow to warm to room temperature and stir for 15 min. The reaction was cooled again to-78 C and a solution of 3-((tert-butyldiphenylsilyl)oxy)propanal (552 mg, 1.77 mmol, 1.0 equiv) in 1.8 mL THF was added by cannula. The reaction was allowed to warm to room temperature and was stirred for 12 hr.10 mL saturated aqueous NH4Cl was added to quench the reaction, followed by 10 mL Et2O, then the aq layer was extracted with Et2O (3 × 10 mL). The combined organic extracts were washed with brine (1 × 10 mL), dried (MgSO4), filtered, and concentrated by rotary evaporation. Purification by silica flash chromatography (10-20% EtOAc/hexanes) yielded the propargyl alcohol as a clear yellow oil (802 mg, 92%). TLC: Rf 0.49 (20% EtOAc/hexanes). 1H-NMR (600 MHz): delta 7.76- 7.64 (m, 4H), 7.56 (t, J = 1.8 Hz, 1H), 7.48- 7.32 (m, 8H), 7.18 (t, J = 7.9 Hz, 1H), 4.92 (td, J = 6.4, 4.3 Hz, 1H), 4.12 (ddd, J = 10.5, 8.2, 3.7 Hz, 1H), 3.89 (ddd, J = 10.3, 5.9, 4.2 Hz, 1H), 3.49 (d, J = 6.4 Hz, 1H), 2.20- 2.07 (m, 1H), 2.03- 1.96 (m, 1H), 1.06 (s, 9H). 13C-NMR (151 MHz): delta 135.5, 134.5, 132.7, 131.5, 130.3, 129.9, 129.7, 127.8, 124.7, 122.0, 91.0, 83.5, 62.2, 61.9, 38.5, 26.8, 19.0.

According to the analysis of related databases, 766-81-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MEMORIAL SLOAN-KETTERING CANCER CENTER; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; THE BROAD INSTITUTE, INC.; UNIVERSITY OF CENTRAL FLORIDA RESEARCH FOUNDATION, INC.; MCKERROW, James; DANDAPANI, Sivaraman; EDWANKAR, Rahul; TAN, Derek, Shieh; FOLEY, Corinne, N.; MOURA-LETTS, Gustavo; VERANO, Alyssa; CHAKRABARTI, Debopam; ROBERTS, Bracken; (258 pag.)WO2017/124087; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 766-81-4,Some common heterocyclic compound, 766-81-4, name is 3-Bromophenylacetylene, molecular formula is C8H5Br, 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.

General procedure: To a solution of 3-substituted-2-haloimidazo[4,5-b]pyridine derivative (1 equiv) in NMP, were added terminal acetylene (1.5 equiv) and tetrabutyl ammonium acetate (1.5 equiv). The solution was purged with nitrogen and stirred at room temperature for 0.15 h, at that time PdCl2(PCy3)2 was added. The reaction solution was purged again with nitrogen and then placed in the microwave and heated for 10 to 30 min at 110 C (for iodide and bromide intermediates). When chloro intermediate was used, the reaction contents were heated at 150 C. When TLC and LCMS showed full consumption of starting materials, the reaction mixture was diluted with ethyl acetate, separated the ethyl acetate layer, given water wash, brine wash and was dried over anhydrous sodium sulphate and concentrated to get the crude material. The crude product was directly purified by column chromatography (0-15% hexane/EtOAc) to isolate the 3-alkyl-2-akynyl imidao[4,5-b]pyridine derivatives.

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

Reference:
Article; Sajith, Ayyiliath M.; Muralidharan; Tetrahedron Letters; vol. 53; 39; (2012); p. 5206 – 5210;,
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. 766-81-4, name is 3-Bromophenylacetylene, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 766-81-4

General procedure: Step1: A mixture of Zn (3 mmol, 196.1 mg, activated by washing with dilute HCl) MeI(6 mmol, 851.6 mg) or EtI (6 mmol, 935.8 mg), phenylacetylene (2 mmol, 204.3mg) and NMP(0.5 mL) was stirred at room temperature until Zn disappeared (~ 2 h). Step 2 CH2Cl2(5 mL) and alpha-ketoneester (0.5 mmol) (oran aldehyde ) wereadded to the mixture of step 1 and the reaction was allowed to proceed at room temperature. After stirredfor ~12 h, the reaction was shown to be complete by TLC. A saturated ammonia chloride solution (10 mL)was added and the organic phase was separated.The water phase was extracted with CH2Cl2. The combined organic phase was washed withsaturated sodium chloride solution and dried with anhydrous sodiumsulfate. After concentration and column chromatograph on silica gel eluted with petroleumether/ethyl acetate (10:1), the product was obtained.

According to the analysis of related databases, 766-81-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhang, Wen; Cao, Yuan; Chen, Wei; Zhao, Gang; Pu, Lin; Tetrahedron Letters; vol. 56; 46; (2015); p. 6430 – 6432;,
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

Application of 766-81-4,Some common heterocyclic compound, 766-81-4, name is 3-Bromophenylacetylene, molecular formula is C8H5Br, 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 nitrogen protection, the product of step 1 and 2.5 equivalents of m-bromophenylacetylene and 0.05 equivalent of cuprous iodide in a solution of diisopropylamine and dichloromethane (volume ratio 1:10) was reacted under nitrogen atmosphere at room temperature for 24 h . The product was isolated on a silica gel column and the yield was 75-80%.

The synthetic route of 766-81-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dalian University of Technology; Ni, Jun; Gai, Xuqiao; Kang, Jiajia; Xu, Liang; (7 pag.)CN105732721; (2016); A;,
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

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

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. 766-81-4, name is 3-Bromophenylacetylene, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H5Br

Step b); Preparation of 1-(3-bromo-phenyl)-2-[5-propionyl-1-(2,2,2-trifluoro-ethyl)-1H-pyrrole-3-yl]-ethane-1,2-dione; A mixture of 1-[4-Iodo-1-(2,2,2-trifluoro-ethyl)-1H-pyrrole-2-yl)-propan-1-one (4.8 g, 0.145 mol), 1-bromo-3-ethynyl-benzene (2.62 g, 0.145 mol) CuI (137 mg, 0.725 mmol) and Pd(PPh3)4 (670 mg, 0.58 mmol) in a mixture of triethylamine (50 ml) and acetonitrile (20 ml) is heated to reflux for 2 hours before cooled down to room temperature. The volatile solvent is removed under reduced pressure, and the residue is partitioned between ethyl acetate (50 ml) and water (200 ml). The organic phase is dried with MgSO4 and is purified by flash chromatography with EtOAc/hexane (10/90-20/80) as eluent to afford the alkyne product as a yellow solid 4.6 g (82%). This solid stirred with KMnO4 (4.73 g, 2.5 mol), NaHCO3 (604 mg, 7.2 mmol) and MgSO4(2.16 g, 18 mmol) in a mixture of acetone (200 ml) and water (100 ml) at room temperature for two hours. The mixture is extracted with ether (2×50 ml) to afford the product as a yellow oil 4.5 g (90%). 1HNMR (DMSO-d6): delta (ppm) 1.03 (t, 3H), 2.92 (q, 2H), 5.38 (q, 2H) 7.56 (t, 1H), 7.74 (s, 1H), 7.92 (d, 1H), 7.95 (d, 2H), 8.06 (s, 1H), 8.12 (s, 1H).

The synthetic route of 766-81-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wyeth; US2007/4786; (2007); 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. 766-81-4, name is 3-Bromophenylacetylene, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 3-Bromophenylacetylene

Step B: 4-[(3-Bromophenyl)ethynyl]-2-chloro-5-fluoropyrimidine; To an oven-dried flask under N2 was added 2,4-dichloro-5-fluoropyrimidine (1.66 g, 10 mmol), anhydrous, degassed THF (100 mL), dichlorobis(triphenyl-phosphine)palladium(II) (180 mg, 0.26 mmol), copper(I) iodide (29 mg, 0.15 mmol), and TEA (2.02 g, 20 mmol). After heating the reaction at 60 C. for 30 min, 1-bromo-3-ethynylbenzene (0.9 g, 5.0 mmol) was added dropwise as a solution in THF (25 mL) and the resulting mixture was allowed to heat overnight. The crude reaction mixture was adsorbed to silica gel and purified by column chromatography (2-10% EtOAc in hexanes) to afford the desired product (1.25 g, 78%) as an off white solid. ESIMS (M+H)+=311.

According to the analysis of related databases, 766-81-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SmithKline Beecham Corporation; US2008/51395; (2008); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 766-81-4,Some common heterocyclic compound, 766-81-4, name is 3-Bromophenylacetylene, molecular formula is C8H5Br, 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 a nitrogen atmosphere,In a 5 mL reaction tube with a Teflon magnetic stir bar,Add 0.015 mmol of cuprous iodide, 0.0075 mmol of 4,4′-di-tert-butyl-2,2′-bipyridine,6.0 mmol of tetrahydrofuran, 3.9 mmol of n-hexane,0.30 mmol 2-chlorophenylacetylene, 0.36 mmol (2-azidoethyl)benzene,0.39 mmol of pentafluoropropionic anhydride, and finally 0.45 mmol of triethylamine,Stir the reaction in a closed system for 15 h at 40 C in an oil bath and then cool to room temperature.Using trifluoromethoxybenzene as an internal standard, the 19F yield was greater than 99%.The organic phases were combined, filtered through 100-200 mesh silica gel and rinsed with dichloromethane.The organic solvent was removed by rotary evaporation to give a crude material.Eluted with n-pentane and dichloromethane (1:1, v/v),6-(2-Chlorophenyl)-3-(pentafluoroethyl)-4-phenylethyl-1,2,4-triazin-5(4H)-one (yield 99%) was obtained.

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

Reference:
Patent; Fuzhou University; Weng Zhiqiang; Wu Wei; (22 pag.)CN109111406; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary