Category: 766-81-4

Application 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.

The catalyst [(IPr) AuCl] (3.1mg, 0.5mol%), 3- bromophenyl acetylene (1mmol), in methanol (1ml) and water (0.5ml) was added successively 25ml reactor.After the reaction mixture was reacted for 6 hours at 110 , cooled to room temperature.Rotary evaporation to remove the solvent, then purified by column chromatography (eluent: petroleum ether / ethyl acetate) to give pure title compound, yield: 93%

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

Reference:
Patent; Nanjing University of Science and Technology; WANG, NANA; MA, JUAN; LI, FENG; (10 pag.)CN106032348; (2016); A;,
Bromide – Wikipedia,
bromide – Wiktionary

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

General procedure: In a glove box filled with nitrogen, to an oven-dried 5 mL pressure tube equipped with a stir bar were added CuI (0.015 mmol, 2.9 mg, 0.050 equiv), 4,4′-di-tert-butyl-2,2′-dipyridine (2.0 mg, 0.0075 mmol, 0.025 equiv), azide compounds (0.36 mmol, 1.2 equiv), terminal alkynes (0.30 mmol, 1.0 equiv), (CF3CF2CO)2O (0.39 mmol, 120.9 mg, 1.3 equiv), Et3N (0.45 mmol, 45.5 mg, 1.5 equiv) and THF/n-C6H14 (1:1, 1.0 mL). The tube was sealed with Teflon screw cap and the solution was stirred at 50 C for 15 h. The reaction mixture was cooled to room temperature and was filtered through a layer of Celite, eluted with dichloromethane. The solvent was removed by rotary evaporation and the resulting product was purified by column chromatography on silica gel with n-pentane/ dichloromethane.

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

Reference:
Article; Lin, Bo; Wu, Wei; Weng, Zhiqiang; Tetrahedron; vol. 75; 19; (2019); p. 2843 – 2847;,
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, Recommanded Product: 766-81-4

(1) by o-methyl nitrobenzene,Zinc powder, acetic acid, water, sodium nitrite, sodium azide, m-bromophenylacetylene, cuprous iodide,The molar ratio of sodium ascorbate to dimethyl sulfoxide is 1: 5: 10: 20: 1: 4: 1: 0.02: 0.1: 70,First1mmol o-nitrobenzene, 5mmol zinc powder, 10mmol acetic acid,20mmol water was added to the reactor, the reaction at room temperature for 9 hours,Subsequently, 1 mmol of sodium nitrite was added to the reactor under an ice-water bath and the reaction was continued for 10 minutes,Then 4mmol sodium azide was added and the reaction was continued for 1 hour,Finally, to the system by adding 1mmol of bromophenyl acetylene,0.02 mmol copper iodide, 0.1 mmol sodium ascorbate,70mmol dimethyl sulfoxide, the reaction 2 hours to obtain the mixed product; (2) Step (1) The resulting mixed product was diluted with 40 mL of water,Then extracted with 400mmol ethyl acetate twice,The extracts were combined and then washed with water and saturated brine each 10mL,Then dried with 2 g of anhydrous sodium sulfate,Under the conditions of a temperature of 35 C and a pressure of 0.03 MPa, the solvent was distilled off under reduced pressure to obtain a crude product,The crude product was further purified by column chromatography (300 mesh silica gel) using ethyl acetate / petroleum ether (ethyl acetate to petroleum ether 1:20 by volume) eluate to give 270 mg of product, yield 86% , The reaction equation is as follows:

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; Kunming University of Science and Technology; Jiang Yubo; Chen Zhen; Zhao Fen; Yang Rui; Xie Kai; Cheng Huiling; (10 pag.)CN104945339; (2017); B;,
Bromide – Wikipedia,
bromide – Wiktionary

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. SDS of cas: 766-81-4

EXAMPLE 26; Preparation of 2-Amino-5-(5-chloro-2-methylthien-3-yl)-3-methyl-5-(3-pyrimidin-5-ylphenyl)-3,5-dihydro-4H-imidazol-4-one; Step a); Preparation of Compound 14; A mixture of 13 (3.17 g, 12.3 mmol), 3-bromophenylacetylene (2.44 g, 13.5 mmol; see MEC00775; dated Aug. 15, 2003), bis(triphenylphosphine)palladium(II) chloride (0.258 g, 0.360 mmol), copper(I) iodide (0.046 g, 0.240 mmol) and triethylamine (3.70 g, 36.8 mmol) in dimethylformamide (60 mL) was stirred at room temperature for 1.5 h. The mixture was diluted with ethyl acetate (300 mL), washed with water (2¡Á100 mL), brine (3¡Á100 mL), dried over sodium sulfate, filtered, and concentrated. The crude material was purified by flash chromatography (silica, hexanes) to afford 14 as a yellow oil, which was a mixture of product and an unidentified by-product (which was removed during purification in the following step): APCI MS m/z 311 [C13H8BrClS+H]+.

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; 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., 766-81-4

Step d); Preparation of Compound 6; A mixture of crude 4 (1.27 g, 4.02 mmol), 3-bromophenyl acetylene 5 (1.10 g, 6.07 mmol) dichlorobis(triphenylphosphino)palladium(II) (0.115 g, 0.164 mmol), copper(I) iodide (0.0248 g, 0.130 mmol), triethylamine (2.19 g, 21.6 mmol) in DMF (20 mL) was stirred at room temperature overnight. The reaction was then diluted with ethyl acetate (500 mL) and washed with water (2¡Á150 mL), 2% aqueous lithium chloride (150 mL), dried over sodium sulfate, filtered, and concentrated. Purification by flash chromatography (silica, 1:19 to 1:9 ethyl acetate/hexanes) afforded 6 (0.376 g, 35%) as a yellow oil: 1H NMR (500 MHz, CDCl3) delta 8.82 (d, J=2.0 Hz, 1H), 7.72 (t, J=1.7 Hz, 1H), 7.60 (d, J=2.0 Hz, 1H), 7.48-7.51 (m, 2H), 7.23 (t, J=8.0 Hz, 1H); ESI MS m/z 264 [C11H6BrNS+H]+.

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; Wyeth; US2007/4786; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding some certain compound to certain chemical reactions, such as: 766-81-4, name is 3-Bromophenylacetylene, 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. 766-81-4

To a mixture of bis(triphenylphosphine)palladium(II) dichloride (134 mg, 0.191 mmol), copper(I) iodide (36 mg, 0.191 mmol) and triethylamine (15 mL) in anhydrous tetrahydrofuran (65 mL) under an atmosphere of argon were sequentially added a solution of 6-iodobenzodioxane (5.00 g, 19.08 mmol) in anhydrous tetrahydrofuran (15 mL) and a solution of (3-bromophenyl)acetylene (3.63 g, 20.03 mmol) in anhydrous tetrahydrofuran (10 mL). The resulting solution was stirred at room temperature for 3 days. The crude mixture was diluted with ethyl acetate, washed sequentially with 1 M hydrochloric acid, water and saturated aqueous sodium hydrogen carbonate, dried over magnesium sulfate and concentrated in vacuo. Purification by column chromatography, using ethyl acetate in heptane (0-15%) as the eluent, gave the title compound in 94% yield: 1H NMR (CDCl3) 5 7.67 (t, J= 1.6 Hz5 1 H), 7.42 – 7.46 (m, 2 H), 7.21 (t, J= 8.0 Hz, 1 H), 7.01 – 7.06 (m, 2 H), 6.84 (d, J= 7.8 Hz, 1 H), 4.26 – 4.31 (m, 4 H); MS (EI) m/z 3U, 316 [M+.].

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 3-Bromophenylacetylene.

Reference:
Patent; ASTRAZENECA AB; ASTEX THERAPEUTICS LTD; WO2008/76046; (2008); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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

In a 100 mL roundbottom flask, LiHMDS (1.0 M in THF, 3.0 mL, 3.0 mmol, 1.1 equiv) was dissolved in 22 mL anhyd hexanes and cooled to 0 C. 1-bromo-3- ethynylbenzene (415 muL, 3.3 mmol, 1.2 equiv) was added and the reaction removed from the cold bath and stirred for 15 min. The reaction was recooled to 0 C, and (R,E)-N-(3-((tert- butyldiphenylsilyl)oxy)propylidene)-2-methylpropane-2-sulfinamide (1.15 g, 2.77 mmol, 1.0 equiv) was transferred via cannula into the reaction in 5.5 mL anhyd hexanes. The reaction was allowed to warm to room temperature with stirring for 12 h. Equal volumes of saturated aqueous NH4Cl and Et2O (20 mL each) were added to the reaction mixture. The layers were separated and the aq layer extracted with Et2O (3 ¡Á 20 mL) then EtOAc (1 ¡Á 20 mL). The combined organic extracts were washed with brine (1 ¡Á 20 mL), dried (Na2SO4), filtered, and concentrated by rotary evaporation. 1H NMR analysis of the crude sample indicated the product was produced in >20:1 d.r. Purification by silica flash chromatography (2:1 hexanes/EtOAc) yielded the N-propargyl sulfinamide as a sticky brown foam (1.05 g, 63%). TLC: Rf 0.47 (40% EtOAc/hexanes). [alpha] D :-10.4 (c 0.55, CHCl3). IR (ATR): 2958, 2931, 2858, 1590, 1556, 1473, 1428, 1111, 1073, 762, 703. 1H-NMR (600 MHz,): delta 7.67 (ddd, J = 8.1, 2.7, 1.4 Hz, 4H), 7.52 (t, J = 1.7 Hz, 1H), 7.44 (ddd, J = 8.0, 2.0, 1.0 Hz, 1H), 7.43- 7.39 (m, 2H), 7.39- 7.33 (m, 4H), 7.32 (dt, J = 7.7, 1.3 Hz, 1H), 7.16 (t, J = 7.9 Hz, 1H), 4.59 (q, J = 6.9 Hz, 1H), 3.91 (ddd, J = 10.5, 6.6, 5.1 Hz, 1H), 3.86 (ddd, J = 10.5, 6.4, 5.1 Hz, 1H), 3.61 (d, J = 7.4 Hz, 1H), 2.11- 1.96 (m, 2H), 1.21 (s, 9H), 1.06 (s, 9H). 13C- NMR (151 MHz,): delta 135.5, 134.4, 133.3, 133.3, 131.5, 130.4, 129.7, 129.6, 127.7, 127.7, 124.6, 122.0, 90.2, 83.6, 60.3, 56.3, 45.6, 39.5, 26.8, 22.5, 19.2. HRMS m/z calcd for C31H38NO2NaSiSBr ([M+Na]+) 618.1474; found 618.1462.

The synthetic route of 3-Bromophenylacetylene has been constantly updated, and we look forward to future research findings.

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

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.

Step 2) 1-Bromo-3-((4-(difluoromethoxy)phenyl)ethynyl)benzene To a solution of 3-bromophenylacetylene (9.1 g, 50.26 mmol), TEA (22.4 g, 221 mmol, 30.8 mL), bis(triphenylphosphine)dichloropalladium(II) (1.41 g, 2.01 mmol), and CuI (230 mg, 1.2 mmol) in DMF (60 mL) was added 4-iodo(difluoromethoxy)benzene (10.85 g, 40.21 mmol) at room temperature. The reaction mixture had gotten warm after the addition was completed. The mixture was stirred for 4 h then the mixture was portioned between EtOAc and water. The aqueous layer was separated and extracted twice with EtOAc. The combined organic layers were dried over Na2SO4, filtered, and concentrated over 40 g Celite. Flash chromatography (SiO2, Hexanes) gave 12 g, 92%, of the title compound as a yellow oil that had crystallized into a solid after being undisturbed for 3d. 1H NMR 500 MHz (DMSO-d6) delta 7.34 (dt, 2H, J=8.92 Hz, 4.70 Hz); 7.42 (t, 1H, 72.99 Hz); 7.54 (t, 1H, J=7.88 Hz); 7.85-7.88 (m, 1H); 7.94-7.97 (m, 1H); 8.00 (dt, 1H, J=8.93 Hz, 4.87 Hz); 8.04 (t, 1H, J=1.80 Hz). Step 2: 1-Bromo-3-((4-(difluoromethoxy)phenyl)ethynyl)benzene To a mixture of 1-bromo-3-ethynylbenzene (9.1 g, 50.26 mmol), TEA (22.38 g, 30.8 mL, 221.1 mmol), PdCl2(ACN)2 (1.41 g, 2.01 mmol) and DMF (60 mL) was added 4-iodo(difluoromethoxy)benzene (10.85 g, 40.21 mmol). The reaction mixture became warm after the addition was completed. The mixture was stirred for 4 h. Then it was poured into water and diluted with EtOAc. The aqueous layer was separated and extracted twice with EtOAc. The combined organic layers were dried over Na2SO4, filtered, and concentrated onto 40 g Celite. Flash chromatography (SiO2, Hexanes) provided 12 g, 92%, of the title compound as a yellow oil that crystallized into a yellow solid upon standing. 1H NMR 500 MHz (CDCl3) delta6.51 (t, J=73.49 Hz, 1H); 7.08 (dd, J=1.27 Hz, 7.65 Hz, 2H); 7.19 (t, J=7.89 Hz, 1H); 7.40-7.46 (m, 2H); 7.47-7.51 (m, 1H); 7.64 (t, J=1.63 Hz, 1H)

According to the analysis of related databases, 3-Bromophenylacetylene, the application of this compound in the production field has become more and more popular.

Reference:
Patent; WYETH; US2009/48320; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary