Category: bromides-buliding-blocks

Some common heterocyclic compound, 108-85-0, name is Bromocyclohexane, molecular formula is C6H11Br, 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. Recommanded Product: 108-85-0

EXAMPLE 7; Entry No. 7-1 to Entry No. 7-6 Following the details given below, effects of various metallic reagents and halides on yield of the products were examined. A mixture of various aromatic zinc reagents shown by ArZnX (X = Br, I) (0.5 M THF solution, 4.0 mL, 2.0 mmol) and magnesium compounds shown by Me3SiCH2MgCl (1.1 M Et2O solution 1.8 mL, 2.0 mmol) was charged in a dry reactor and stirred at 0C for 0.5-1 hour. To the solution obtained, TMEDA (0.30 mL, 2.0 mmol), various halides (shown by “(FG)Ralkyl-X” in TABLE 6) (1.0 mmol) and then FeCl3 (0.1 M THF solution, 0.5 mL, 0.05 mmol) were added at 0C. The reaction mixture was stirred at 30C for 6 hours. Saturated NH4Cl aqueous solution was added to terminate the reaction. The mixture was filtered through a pad of Florisil (registered trademark) and concentrated in vacuum. The residue was purified by silica gel chromatography Entry No. 7-4 (4-Cyclohexylbenzonitrile) Halide: 3-bromocyclohexane (1.0 mmol) Aromatic zinc reagent: 4-cyanophenylzinc bromide (2.0 mmol) Reaction time: 6 hours Colorless oily substance (167 mg, 90%) FTIR (neat): cm-1 2925 (s), 2852 (m), 2227 (m), 1607 (m), 1505 (m), 1449 (m), 1415 (w), 1177 (w), 1000 (w), 823 (s); 1H NMR (500 MHz, CDCl3): delta 7.56 (d, J = 8.6 Hz, 2H), 7.30 (d, J = 8.6 Hz, 2H), 2.12-2.00 (m, 1H), 1.92-1.80 (m, 4H), 1.80-1.69 (m, 1H), 1.47-1.33 (m, 4H), 1.33-1.20 (m, 1H); 13C NMR (125 MHz, CDCl3): delta 153.4, 132.1 (2C), 127.6 (2C), 119.1, 109.5, 44.7, 33.9 (2C), 26.6 (2C), 25.9; Elemental analysis: Calcd. for C13H15N: C, 84.28; H, 8.16; N, 7.56. Found: C, 84.12; H, 8.36; N, 7.36.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 108-85-0, its application will become more common.

Reference:
Patent; Japan Science and Technology Agency; EP1724248; (2006); A1;,
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Reference of 68322-84-9, 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. 68322-84-9, name is 2-Bromo-1-fluoro-4-(trifluoromethyl)benzene, This compound has unique chemical properties. The synthetic route is as follows.

Intermediate 8: Preparation of 5-Cyano-5-(4-methoxy-8-trifluoromethyl- dibenzofuran-l-yl)-2-oxo-cyclohexanecarboxylic acid methyl esterStep-1: Preparation of 3-(2-Bromo-4-trifluoromethyl-phenoxy)-4-methoxy- benzaldehydeTo a stirred solution of Isovanillin (5 gm, 0.0328 moles) and Potassium carbonate (13.6 gm, 0.0985 moles) in dry DMF (20 ml) was added 3-Bromo-4- Fluorobenzotrifluoride (8.065 gm, 0.0331 moles) over a period of 15 min at room temperature under nitrogen atmosphere, and then above reaction mixture was stirred at 14O0C for 5 hrs. After completion of reaction, the reaction mixture was cooled to room temperature and the contents were poured in to water (100 ml) and extracted with ethyl acetate (3XlOOmI). The organic extracts were combined and washed with IN sodium hydroxide, water and brine, dried with sodium sulfate, filtered and solvent evaporated under vacuum to obtain the title compound (11.58 gm, yield-94%) a pale yellow solid.1H NMR (300 MHz, CDCl3) delta 3.92 (s, 3H), 6.75 (d, J= 8.6 Hz, IH), 7.15 (d, J= 8.5 Hz, IH), 7.45 (d, J= 8.6 Hz, IH), 7.54 (d, J = 1.9 Hz, IH), 7.77 (dd, J=8.4 Hz, J=I.9Hz, IH,), 7.90 (s, IH), 9.87 (s, IH)MS (M++.): 376

The chemical industry reduces the impact on the environment during synthesis 2-Bromo-1-fluoro-4-(trifluoromethyl)benzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MATRIX LABORATORIES LTD.; WO2009/115874; (2009); A2;,
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Application of 61326-44-1,Some common heterocyclic compound, 61326-44-1, name is 1,1,2,2-Tetrakis(4-bromophenyl)ethene, molecular formula is C26H16Br4, 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 present invention is preferably 1,1,2,2-tetrakis(4-bromophenyl)ethylene: 1H-1,2,4-triazole: potassium carbonate: copper oxide molar ratio of 2: 10-15: 30: 1; Reaction temperature of 100 deg.C. The reaction time was 48 hours. In a polar solvent, using the “one-pot method”, 1,1,2,2-tetrakis(4-bromophenyl)ethylene,1H-1,2,4-triazole, potassium carbonate and copper oxide under heating conditions 1,1,2,2-tetrakis[4-(1H-1,2,4-triazol-1-yl)phenyl]ethylene (L) is prepared. Yield 60percent.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,1,2,2-Tetrakis(4-bromophenyl)ethene, its application will become more common.

Reference:
Patent; Tianjin Normal University; Wang, Ying; (12 pag.)CN105669705; (2016); A;,
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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, Application In Synthesis of 2′-Bromophenylacetylene

To a 10 mL screw cap vial, 2-bromophenylacetylene (0.5 mmol) and a solution of azidopentafluoroethane in THF (?0.60 mmol, 3-4 mL) were added. An aqueous solution of CuSO4-5H2O (1 mol·l-1, 0.05 mmol, 50 mul) and sodium L-ascorbate (1 mol·l-1, 0.05 mmol, 50 mul) were added, the vial was closed and the content was stirred at rt for 18 h. Saturated aqueous NH4Cl (10 mL) was added and the product was extracted into CH2Cl2 (3*10 mL). The combined organic phase was washed with water (2*10 mL), dried (MgSO4), filtered and solvent was removed under reduced pressure. Purification by column chromatography (silicagel) gave pure product as a white solid. Yield 37%; Rf (cyklohexane:EtOAc 95:5)=0.53; IR (CHCl3, film) v=1430, 1210, 1128, 1077, 972 cm; 1H NMR (400 MHz, CDCl3) delta=8.63 (s, 1H), 8.15 (dd, J=7.8, 1.7 Hz, 1H), 7.70 (dd, J=8.1, 1.2 Hz, 1H), 7.47 (td, J=7.6, 1.3 Hz, 1H), 7.29 (td, 1H); 13C NMR (101 MHz, CDCl3) delta=146.4, 133.9, 131.1, 130.6, 129.4, 128.1, 121.6, 121.4, 117.2 (qt, 1JC-F=287.5 Hz, 2JC-F=41.2 Hz, CF3), 110.3 (tq, 1JC-F=271.4 Hz, 1JC-F=43.2 Hz, CF2); 19F NMR (376 MHz, CDCl3) delta=-84.4 (s, 3F), -99.2 (s, 2F); HRMS (ESI) m/z calculated for C10H6N3BrF5 [M+H]+: 341.9660, found 341.9661.

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:
Patent; Ustav organicke chemie a biochemie AV CR, v.v.i.; CF Plus Chemicals s.r.o.; BEIER, Petr; MATOUSEK, Vaclav; BLASTIK, Zsofia E.; VOLTROVA, Svatava; (12 pag.)US2019/161452; (2019); A1;,
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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. 40161-54-4, name is 1-Bromo-2-fluoro-4-(trifluoromethyl)benzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: bromides-buliding-blocks

To a solution of 4-bromo-3-fluoro-benzotrifluoride (585 mg, 2.36 mmol) in 15 mL of THF, stirred at -75 C. under nitrogen atmosphere, 1.53 mL (2.6 mmol) of a 1.7M solution of tert-butyllithium in pentane were added dropwise. The reaction mixture was stirred at -60 C. for 15 minutes then a solution of 2-methyl-propane-2-sulfinic acid-(tetrahydro-pyran-4-ylidene)-amide (400 mg, 1.97 mmol; prepared as described in literature: WO2005/87751 A2) in 10 mL of THF was added dropwise. The reaction mixture was allowed to reach room temperature and stirred for 1 hr. A saturated ammonium chloride solution was added and the reaction mixtures was extracted with ethyl acetate. The organic phases were collected, dried over sodium sulfate and concentrated under vacuum. The crude obtained was purified by flash chromatography (eluent: cyclohexane/AcOEt; gradient from 12% to 100% of AcOEt). The oil obtained was diluted in 2 mL of 1,4-dioxane, 0.4 mL of a 4 M solution of hydrochloric acid in 1,4-dioxane were added, the reaction mixture was stirred at room temperature for 1 hr and then concentrated under vacuum to obtain 100 mg of the title compound as white solid.LC-MS (Method 2): Rt=0.90 minMS (ESI pos): m/z=264 (M+H)+

The synthetic route of 40161-54-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boehringer Ingelheim International GmbH; HOENKE, Christoph; BERTANI, Barbara; FERRARA, Marco; FOSSATI, Giacomo; FRATTINI, Sara; GIOVANNINI, Riccardo; HOBSON, Scott; (88 pag.)US2017/101411; (2017); A1;,
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67567-26-4, name is 4-Bromo-2,6-difluoroaniline, belongs to bromides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. name: 4-Bromo-2,6-difluoroaniline

Example 1 5-Bromo-1,3-difluoro-2-nitro-benzene: To a suspension of sodium perborate tetrahydrate (1.04 g, 5 mmol) in acetic acid (20 m]L), stirred at 55 C., was added a solution of 4-bromo-2,6-difluoroaniline in acetic acid (10 mL) over 1 hour in a dropwise fashion. After stirring at 55 C. for an additional 3 hours, the solution was allowed to cool to room temperature and filtered. The filtrate was poured into ice, and extracted twice with ethyl acetate. The combined organic extracts were washed successively with 5*100-mL portions of water, brine, dried (MgSO4), and concentrated in vacuo. The resulting residue was purified by column chromatography over silica gel eluted with ethyl acetate:hexanes (1:20) to afford 780 mg of the titel compound as a tan solid. 1H NMR (CDCl3) delta 7.32 (dt, 2H).

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

Reference:
Patent; Charifson, Paul S.; Deininger, David D.; Grillot, Anne-Laure; Liao, Yusheng; Ronkin, Steven M.; Stamos, Dean; Perola, Emanuele; Wang, Tiansheng; LeTiran, Arnaud; Drumm, Joseph; US2005/256136; (2005); A1;,
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Related Products of 3344-70-5, These common heterocyclic compound, 3344-70-5, name is 1,12-Dibromododecane, 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.

1.0 g of compound 3,2.63 g of 1,12-dibromododecane,0.43 g of potassium hydroxide and 0.16 g of tetrabutylammonium bromide,Was added to a mixture of 10 ml of dichloromethane and 6.5 ml of water,The mixture was stirred at room temperature under nitrogen for 24 hours,Washed twice with 30 ml of water,Washed once with 15 ml of saturated brine,The organic layer was separated,After adding anhydrous sodium sulfate to remove water,The solvent was removed on a rotary evaporator,(200: 300 mesh silica gel column chromatography elution (ethyl acetate / petroleum ether volume ratio of l: 30-l: 10),To give 1.19 g of the compound 4 as a pale yellow liquid,Yield 90percent.

Statistics shows that 1,12-Dibromododecane is playing an increasingly important role. we look forward to future research findings about 3344-70-5.

Reference:
Patent; Guilin University of Technology; Kong, Xiangfei; Dai, Shengping; Chang, Xiao; Zhang, Laiqi; Wang, Guixia; (10 pag.)CN106117220; (2016); A;,
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Related Products of 766-46-1, The chemical industry reduces the impact on the environment during synthesis 766-46-1, name is 2′-Bromophenylacetylene, I believe this compound will play a more active role in future production and life.

General procedure: To a solution of sulfonyl azides 1 (0.6 mmol), o-bromo-phenylacetylenes 2 (0.5 mmol), aromatic amines 3 (0.55 mmol), and CuI (0.05 mmol) in DMSO (2 mL) in Schlenk tube was added TEA (0.5 mmol) slowly via a syringe. The reaction solution was stirred at room temperature under N2 for 2 h. The solution was then added to CuI (0.05 mmol), K2CO3 (1 mmol), and l-proline (0.2 mmol), and the mixture was stirred at 60 C under N2 for 4 h. The reaction mixture was partitioned between ethyl acetate and saturated aq NH4Cl, the organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography on silica gel with petroleum ether and ethyl acetate (6:1 to 9:1).

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; Jin, Hongwei; Zhou, Bingwei; Wu, Zhi; Shen, Yang; Wang, Yanguang; Tetrahedron; vol. 67; 6; (2011); p. 1178 – 1182;,
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These common heterocyclic compound, 5469-19-2, name is 1-Bromo-2,4,5-trimethylbenzene, 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. name: 1-Bromo-2,4,5-trimethylbenzene

c. N,N,,N”,N”‘-(4,4,,4″,4,”-methanetetrayltetrakis(benzene-4, 1 – diyl))tetrakis(2,4,5-trimethyl-N-(2,4,5-trimethylphenyl)aniline) In a dry box, 4,4’,4″,4″‘-methanetetrayltetraaniline (1 .00 g, 3.08 mmol), 1 – bromo-2,4,5-trimethylbenzene (1 .35 g, 3.67 mmol), tris(tert- butyl)phosphine (0.1 0 g, 0.50 mmol) and Pd2(DBA)3 (0.23 g, 0.25 mmol) were combined in round bottom flask and dissolved in 120 ml of dry toluene. The solution was stirred for a minute and followed by sodium tert- butoxide (2.72 g, 28.33 mmol) and 5 ml of dry toluene. A heating mantle was added and the reaction heated to 80C for 18 hour. More 1 -bromo- 2,4,5-trimethylbenzene (350mg) and NaOtBu (180mg) were added and the reaction stirred at 80C for another 24 hour. The reaction mixture was then cooled to room temperature and filtered, washing with toluene (200 mL). The solvent was removed by rotary evaporation and the residue was re-dissolved in chloroform (40ml_). The crude product was precipitated into methanol (300ml_) and collected (3.3g, 85% pure) by filtration. The crude product was purified further by silica gel column chromatography using a gradient of chloroform in hexanes (5-21 %). Recrystallization from chloroform and ethanol yielded 2.60 g (64%) of product as a pale yellow solid. 1 H NMR (CDCI3) is consistent with structure for Compound 2.

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

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; WANG, Ying; WU, Weishi; DOBBS, Kerwin, D.; WO2011/49904; (2011); A2;,
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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. 452-63-1, name is 1-Bromo-4-fluoro-2-methylbenzene, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 452-63-1

Intermediate 2:; 4-Fluoro-2-methvl-benzaldehvde; 2-Bromo-5-fluorotoluene (15.0 g, 79.3 mmol) was dissolved in anhydrous THF andcooled to -78C in an acetone/dry ice bath. N-butyl-lithium (48.0 mL, 119 mmol) was addeddropwise down the side of the reaction flask and the resulting solution was stirred for 10 min. 64.0 ml of anhydrous DMF (793 mmol) was then added in the same fashion. After 1 hour, the reaction was quenched with cold aqueous NH4CI and diluted with 500 mL Et2O and washed with water (3x 300 mL)., The organic layer was dried over MgS04, filtered and concentrated under reduced pressure. The crude material was then equipped with a distillation apparatus and the oil bath was heated to 110 C. Product containing fractions were collected to give a colorless oil, (10.0 g , 72.4 mmol, 92% yield); LRMS m/z (APCI+) 139 [M+ H]; 400 MHz 1HNMR (CDCI3) 8 10.91 (s, 1H); 7.81 (dd, J=6.2, 2.5 Hz, 1H); 7.03 (ddd, J=8.2, 8.2, 2.5 Hz, 1H); 6.95 (ddd, J=9.5, 2.5, 0.0 Hz, 1H); 2.67 (s, 3H).

According to the analysis of related databases, 452-63-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2004/110996; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary