Category: bromides-buliding-blocks

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. 827-08-7, name is 1,2-Dibromo-3,4,5,6-tetrafluorobenzene, A new synthetic method of this compound is introduced below., Formula: C6Br2F4

4-Bromo-5-methyl-2-phenylthiazole6 (1.2 g, 4.7 mmol) was dissolved in anhydrous THF (20 mL) under argon atmosphere. 1.6 M n-BuLi hexane solution (3.0 mL, 4.8 mmol) was slowly added dropwise to the solution at -78 C, and the mixture was stirred for 1.5 h. Tri-n-butyl borate (1.3 mL, 4.8 mmol) was slowly added to the solution at the temperature, and the mixture was stirred for 2.5 h. An adequate amount of distilled water was added to the mixture to quench the reaction. 1,2-Dibromotetrafluorobenzene (640 mg, 2.1 mmol), tetrakis(triphenylphosphine)palladium(0) (160 mg, 0.14 mmol), and 20 wt% Na2CO3 aqueous solution (7.5 mL) were added to THF (30 mL), and the mixture was refluxed for 6 h. The reaction mixture was neutralized by HCl aqueous solution, extracted with ether, washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The crude product was purified by column chromatography on silica gel using n-hexane as the eluent to give 160 mg of 2a in 15% yield based on 1,2-dibromotetrafluorobenzene. The 1H and 13C NMR spectra of 2a are shown in Figure S1. 2a: 1H NMR (300 MHz, CDCl3, TMS) delta = 2.29 (s, 6H, CH3), 7.27-7.37 (m, 6H, Aromatic H), 7.67-7.73 (m, 4H, Aromatic H). 13C NMR (75 MHz, CDCl3) delta = 12.1, 126.3, 128.9, 129.9, 133.4, 133.5, 142.7, 164.5. HR-MS (MALDI) m/z = 497.0762 (MH+). Calcd for C26H17F4N2S2+ = 497.0764.

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:
Article; Hamatani, Shota; Kitagawa, Daichi; Kobatake, Seiya; Nakahama, Tatsumoto; Tetrahedron Letters; (2020);,
Bromide – Wikipedia,
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Some common heterocyclic compound, 113170-72-2, name is 3-Bromo-5-(trifluoromethyl)benzene-1,2-diamine, molecular formula is C7H6BrF3N2, 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: 113170-72-2

Na2S2O5 (1.64 g, 8.62 mmol) and 4-fluoro-benzaldehyde (891 mg, 7.18 mmol) were added to a sol. of 3-bromo-5-trifluoromethyl-l,2-diaminobenzene (1.65 g, 6.47 mmol) – -in DMA (40 ml). The r.m. was stirred overnight at 70 0C. Then, the r.m. was cooled to r.t. and poured into water. The solid was filtered off, washed with water, and suspended in DIPE and some drops of 2-propanol. The resulting solid was filtered off, washed with DIPE, and dried. Yield: 1.95 g of intermediate 64 (84 %).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 113170-72-2, its application will become more common.

Reference:
Patent; ORTHO-MCNEIL-JANSSEN PHARMACEUTICALS, INC; GIJSEN, Henricus, Jacobus, Maria; VELTER, Adriana, Ingrid; MACDONALD, Gregor, James; BISCHOFF, Francois, Paul; WU, Tongfei; VAN BRANDT, Sven, Franciscus, Anna; SURKYN, Michel; ZAJA, Mirko; PIETERS, Serge, Maria, Aloysius; BERTHELOT, Didier, Jean-Claude; DE CLEYN, Michel, Anna, Jozef; OEHLRICH, Daniel; WO2010/89292; (2010); A1;,
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Related Products of 40161-54-4, 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.

(Step 3) Synthesis of 2-(2-fluoro-4-(trifluoromethyl)phenyl)-1-methyl-5-(4-(trifluoromethypplicnyl)-1H-imidazole 3-oxide (Compound 1-5) 1.0 g (4.1 mmol, 1.1 eq) of 1-methyl-5-(4-(trifluoromethyl)phenyl)-1H-imidazole 3-oxide, 0.043 g (0.19 mmol, 5 mol %) of palladium acetate, 0.18 g (0.57 mol, 15 mol %) of tri(p-fluorophenyl)phosphine, 0.11 g (1.1 mmol, 30 mol %) of pivalic acid, and 1.0 g (7.4 mmol, 2.0 eq) of carbonic acid potassium were added to a reactor, followed by replacing the air with argon gas. 14 mol of anhydrous acetonitrile solution of 0.90 g (3.7 mmol, 1.0 eq) of 4-bromo-3-fluorobenzene trifluoride was added to the resulting mixture, followed by stirring over night at 70 C. The resulting reaction liquid was filtered over celite and concentrated under reduced pressure. The obtained crude crystal was washed with diethylether to obtain 1.1 g of the objective compound (yield: 73%). 1H-NMR of the obtained compound is shown below: 1H-NMR (400 MHz, CDCl3): delta 8.21(m, 1H), 7.80(m, 2H), 7.64(m, 111), 7.59(m, 2H), 7.57(m, 1H), 7.47(s, 1H), 3.57(d, 3H).

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, 1-Bromo-2-fluoro-4-(trifluoromethyl)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Nippon Soda Co., Ltd.; AOYAMA, Hikaru; MATSUI, Maki; IWASA, Takao; FUJII, Kazushige; KOBAYASHI, Tomomi; SAKANISHI, Keita; (32 pag.)US2017/223958; (2017); A1;,
Bromide – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 1073-06-9, name is 1-Bromo-3-fluorobenzene, 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 1073-06-9, Formula: C6H4BrF

Diacetoxypalladium (3.3 mg, 0.01 mmol) was added to a stirred mixture of methyl 2-morpholino-4-oxo-8-[(2R)-pyrrolidin-2-yl]chromene-6-carboxylate (121 mg, 0.34 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (16.61 mg, 0.03 mmol), 1-bromo-3-fluorobenzene (0.047 mL, 0.42 mmol) and cesium carbonate (165 mg, 0.51 mmol) suspended in 1,4-dioxane (3.3 mL). The resulting suspension was degassed with argon and then stirred at 100 C. for 20 h. The reaction mixture was allowed to cool to room temperature, and the crude product was purified by flash chromatography on silica gel eluting with 0 to 7% propanol in DCM. The solvent was evaporated to dryness to afford methyl 8-[(2R)-(1-(3-fluorophenyl)pyrrolidin-2-yl)]-2-morpholino-4-oxo-4H-chromene-6-carboxylate (120 mg, 79%) as a yellow oil which solidified on standing. Mass Spectrum: m/z [M+H]+=453.

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, 1-Bromo-3-fluorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; US2012/264731; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 399-94-0, A common heterocyclic compound, 399-94-0, name is 1-Bromo-2,5-difluorobenzene, molecular formula is C6H3BrF2, 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.

Description 14:; 2-Bromo-3,6-difluorobenzaldehyde (D14)To solution of diisopropylamine (13.29 mL, 93 mmol) in THF (300 mL) at -78 0C, was added n-butyllithium (34.2 mL of 2.5M in hexanes, 85 mmol), dropwise over 10 mins. The mixture was stirred at -78 0C for 15 mins and then 2-bromo-1 ,4-difluorobenzene (15 g, 78 mmol) in THF (100 mL) was added dropwise over 15 mins maintaining the temperature below -65 C. After stirring for 1 hr at -78 0C, N,N-dimethylformamide (6.62 mL, 85 mmol) was added via syringe. The mixture was stirred at -78 0C for 30 mins and then quenched with sat. NH4CI solution and the mixture was allowed to reach room temperature. The product was extracted into ether and the extracts were dried (Na2SO4) and evaporated. Chromatography (silica, 0-100% dichloromethane in hexane) gave the title compound(D14) as a yellow solid (12.73 g)NMR (deltaH), (CDCI3): 7.16 (1 H, m), 7.35 (1 H, m), 10.32 (1 H, s).

The synthetic route of 399-94-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/107455; (2008); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 174508-31-7, These common heterocyclic compound, 174508-31-7, name is 5,7-Dibromo-2,3-dihydrothieno[3,4-b][1,4]dioxine, 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 (2),4-pyridylboronic acid pinacol ester (2.01 g, 9.8 mmol),Tetrakis(triphenylphosphine)palladium (407 mg, 0.352 mmol),Potassium phosphate (5.95 g, 28 mmol) was added to a 250 mL flask.Add 70 mL of Compound 4 (1.08 g, 3.61 mmol) in a nitrogen atmosphere.1,4-dioxane solution,The reaction solution is heated to 90 C,Reaction 72h,After the reaction is completed, cool to room temperature.filter,The filter residue is washed with chloroform.The filtrate was spun in a rotary evaporator.After that, it was purified by silica gel column chromatography (eluent was a mixture of chloroform_methanol=200:1).Purification gives a yellow solid, compound 5,Yield 60%;

The synthetic route of 174508-31-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; South University of Science and Technology of China; Su Fengyu; Wu Xiaowen; Tian Yanqing; Liu Yanjun; Luo Dan; Sun Xiaowei; (16 pag.)CN108997427; (2018); A;,
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Application of 51554-93-9,Some common heterocyclic compound, 51554-93-9, name is 1-Bromo-4-octylbenzene, molecular formula is C14H21Br, 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: 1-Bromo-4-methylbenzene (1.0 g, 5.88 mmol) was dissolved in 30 mL anhydrous THF under argon. The solution was cooled to -78 C before solution of n-BuLi (2.4 M) in hexane (3.4 mL, 8.16 mmol) was added dropwise. The reaction mixture was stirred for 10 min at -78 C. 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.9 g, 10.2 mmol) was added then. The reaction mixture was allowed to warm up to room temperature and stirred overnight before it was poured into ice water. The solution was extracted with 100 mL dichloromethane (CH2Cl2), the organic layer washed with 70 mL brine and dried with Na2SO4 before the solvent was removed. The crude product was purified by column chromatography on silica gel with petroleum ether/CH2Cl2 (10:1, v/v) as an eluent to give a white solid (1.1 g, 85% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-4-octylbenzene, its application will become more common.

Reference:
Article; Zhu, Minliang; Luo, Hao; Wang, Liping; Guo, Yunlong; Zhang, Weifeng; Liu, Yunqi; Yu, Gui; Dyes and Pigments; vol. 98; 1; (2013); p. 17 – 24;,
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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. 345965-54-0, name is 1-(4-Bromophenyl)cyclopropanamine, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1-(4-Bromophenyl)cyclopropanamine

To a solution of 1 -(4-bromophenyl)cyclopropanamine (534 mg, 2.52 mmol) and DIPEA (0.66 mL, 3.77 mmol) in anhydous THF (10 mL) was added 2-methoxybenzoyl chloride (0.41 mL, 2.77 mmol) at 0 C. The reaction mixture was then allowed to return to room temperature and stirred overnight. The mixture was quenched with a saturated solution of ammonimum chloride (20 mL), extracted with EtOAc (3 x 10 mL). The combined organic extracts were washed with water (2 x 10 mL), brine (10 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. Further purification by flash column chromatography (heptane/EtOAc 90:10 to 60:40) gave Lambda/-[1 -(4- bromophenyl)cyclopropyl]-2-methoxy-benzamide (362 mg,1 .05 mmol, 42% yield) as a white fluffy solid. UPLC-MS (ES+, Short acidic): 1 .98 min, m/z 346.1 [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 345965-54-0.

Reference:
Patent; REDX PHARMA PLC; GUISOT, Nicolas; (191 pag.)WO2017/46604; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 34699-28-0, name is 1-(4-Bromophenyl)-1,2,2-triphenylethylene, 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 34699-28-0, HPLC of Formula: C26H19Br

2, 250ml three-necked flask was evacuated and filled with N2 three times, 10mmol of Compound 1-1 was added, 120ml of water after drying and discharged air tetrahydrofuran,Under conditions of -78 C, 12 mmol n-butyllithium was slowly added and stirred for 3 hours Slowly into 21mmol trimethyl borate, return to room temperature, stirred for 12 hours, 10ml hydrochloric acid was added to terminate the reaction, the organic phase Extract with CH2Cl2, extract the organic layer three times with saturated brine, dry the combined organic phases over anhydrous Na2SO4, spin-off Organic solvents, column chromatography gave the product 1-2 as a white solid. Yield: 81.6%

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; Jiangxi Science and Technology Normal University; Pu Shouzhi; Chen Zhao; Liu Gang; Zhao Fei; (11 pag.)CN107082753; (2017); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 393-37-3, These common heterocyclic compound, 393-37-3, name is 5-Bromo-2-fluorobenzotrifluoride, 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.

To a solution of 4-bromo-l-fluoro-2-(trifluorom ethyl )benzene (5.0 g, 20.5 mmol, 2.9 mL) in THF (50.0 mL) was added LDA (2 M, 13.3 mL) at -78C. The mixture was stirred at -78C for 1 hr. Then DMF (1.8 g, 24.6 mmol, 1.9 mL) was added and stirred for 1 h at -78C. The mixture was poured into Sat H4C1 (20.0 mL) and extracted with ethyl acetate (20.0 mL x 3). The combined organic layers were washed with brine (20.0 mL x 3), dried over Na2S04, filtered and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography (Si02, Petroleum ether / Ethyl acetate = 1/0 to 10/1) to afford 5-bromo- 2-fluoro-3-(trifluoromethyl)benzaldehyde (4 g, 14.7 mmol, 71.7% yield). 1H MR (CHLOROFORM-d, 400 MHz): delta 10.35 (s, 1H), 8.19 (dd, J= 2.5, 5.4 Hz, 1H), 7.98 (dd, J= 2.1, 6.1 Hz, 1H).

The synthetic route of 393-37-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; QUENTIS THERAPEUTICS, INC.; VACCA, Joseph P.; LI, Dansu; BETTIGOLE, Sarah; (184 pag.)WO2018/222918; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary