Author: Jessica.F

Application of 608-30-0,Some common heterocyclic compound, 608-30-0, name is 2,6-Dibromoaniline, molecular formula is C6H5Br2N, 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 18 4-tert-butyl-N-(2,6-dibromophenyl)benzamide: 2,6-Dibromoaniline (1.0 g, 3.98 mmol) was dissolved in dioxane (20 mL) and treated with diisopropylethylamine (1.39 mL, 7.96 mmol) followed by 4-tert-Butylbenzoyl chloride (1.70 g, 7.96 mmol). The solution was warmed to 60 C. and stirred overnight. The mixture was concentrated under reduced pressure and the residue was re-dissolved in ethyl acetate (50 mL). The organic solution was washed with 10% HCl (2*50 mL), saturated sodium carbonate (50 mL) and saturated sodium chloride (50 mL). The organic layer was dried (magnesium sulfate), filtered, and concentrated under reduced pressure. The residue was purified by flash silica gel chromatography, eluding with 20% acetone/hexane to yield 1.33 g (81%) of product. MS (ESI) m/z 409.9772; HPLC Method B, purity 92.3% at 210-370 nm, 10.4 min.; 89.7% at 232 nm, 10.4 min.; HRMS: calcd for C17H17Br2NO+H+, 409.97496; found (ESI, [M+H]+), 409.9772.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,6-Dibromoaniline, its application will become more common.

Reference:
Patent; Wyeth; US2006/264631; (2006); 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. 345965-54-0, name is 1-(4-Bromophenyl)cyclopropanamine, This compound has unique chemical properties. The synthetic route is as follows., category: bromides-buliding-blocks

A solution of 1-(4-bromophenyl)-cyclopropylamine (Intermediate 116, 244.0 mg, 1.15 mmols) and benzyl bromide (255.0 mg, 1.50 mmols) in 4 mL DMF was stirred at 85 C. for 6 hours, cooled to room temperature and stirred overnight. The solution was diluted with H2O and the pH adjusted to 8-9 with aqueous NaOH. The solution was extracted with EtOAc and the combined organic layers were washed with H2O and saturated aqueous NaCl, dried (MgSO4) and concentrated under reduced pressure. Column chromatography (5-10% EtOAc-Hexanes) afforded 110 mg (32%) of the N-benzyl amine. 1H NMR (CDCl3) delta: 7.48 (2H, d, J=8.4 Hz), 7.30-7.23 (7H, m), 3.68 (2H, s), 1.07 (2H, m), 0.93 (2H, m); and 100 mg (22%) of the N,N-dibenzyl amine, 1H NMR (CDCl3) delta: 7.55 (2H, d, J=8.3 Hz), 7.40-7.19 (12H, m), 3.61 (4H, s), 0.87 (2H, m), 0.71 (2H, m).

According to the analysis of related databases, 345965-54-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Allergan Sales, Inc.; US6313107; (2001); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

7073-94-1, name is 1-Bromo-2-isopropylbenzene, 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. Formula: C9H11Br

29.87 g 1-bromo-2-isopropyl benzene and 23.6 g 2-naphthylamine were added into a dry 2 L three-neck flask, followed by adding 600 mL dry and degassed toluene to dissolve. Then, 43.2 g sodium tert-butoxide (3.0 eq.), 0.7 g catalyst palladium diacetate (2% mol) and 3.7 g 1,1?-binaphthyl-2,2?-bis(diphenylphosphino) (BINAP, 4% mol) ligand were added. The reaction mixture was heated up to 110 C. and reacted overnight. After the reaction finished and the reaction mixture was cooled down to room temperature. The residual was absorbed by the added activated carbon, filtered by suction filtration and removed with solvent by rotary evaporation, followed by recrystallization with a mixture of toluene and ethanol, to produce 34.5 g Intermediate (18) at a yield of 88%.

The synthetic route of 7073-94-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NANJING TOPTO MATERIALS CO.,LTD.; KIM, JIN WOO; QIAN, CHAO; GAO, PENGHUI; WANG, XIAOWEI; (157 pag.)US2018/105534; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 1798-85-2, 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. 1798-85-2, name is 1-Bromo-3-cyclopropylbenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A Schlenk flask was charged with an appropriate amount of complex 2b (0.016mmol, 2.0mol%) and the corresponding bromo or iodo arene (0.77mmol). The flask was cycled with nitrogen and vacuum. Afterwards a THF solution of benzylzinc bromide (2.2mL, 1.1mmol, 0.5M in THF) was added. The flask was sealed and heated at 70C for 24h. After that time, the mixture was cooled, and dichloromethane and water were added. The aqueous layer was extracted with dichloromethane and the collected organic layers were washed with water and dried with Na2SO4. The coupling product was confirmed by GC-MS (with n-dodecane as internal standard) and NMR analysis. The analytical properties of the products are in agreement with literature data [6a,24].

The synthetic route of 1-Bromo-3-cyclopropylbenzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Someya, Chika I.; Irran, Elisabeth; Enthaler, Stephan; Inorganica Chimica Acta; vol. 421; (2014); p. 136 – 144;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 1003-98-1,Some common heterocyclic compound, 1003-98-1, name is 2-Bromo-4-fluoroaniline, molecular formula is C6H5BrFN, 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 an ice-cooled mixture of 2-bromo-4-fluoroaniline (25.0 g, 0.132 mol), ammonium thiocyanate (40.0 g, 0.525 mol) in acetic acid (180 mL) was added dropwise a solution of bromine (13.5 mL, 0.264 mol) in acetic acid (35 mL) over 1 h. After stirring at room temperature for 2 h, the yellow insoluble material was collected by filtration. The yellow cake was suspended in water, and the pH was adjusted to 11 by adding potassium carbonate. The insoluble material was collected again, and the cake was purified by flash column chromatography on silica gel (Hexane:AcOEt = 3:1) to give the title compound as a yellow solid (29.7 g, 91%). Mp 183-185 C. 1H NMR (400 MHz, DMSO-d6) delta 7.37 (1H, dd, J = 8.5, 2.4 Hz), 7.64 (2H, dd, J = 8.5, 2.4 Hz), 7.82 (2H, brs). 13C NMR (100 MHz, DMSO-d6) delta 107.5 (d, J = 27.8 Hz), 109.4 (d, J = 11.5 Hz), 116.0 (d, J = 26.8 Hz), 131.8 (d, J = 11.5 Hz), 147.7 (d, J = 1.9 Hz), 156.2 (d, J = 239.6 Hz), 166.8. IR (ATR) nmax 3079, 1634, 1539, 1452, 1394, 1319, 1208, 1099, 1057, 940, 847 cm-1. MS (EI) 246 (M+). HRMS (EI) calcd for C7H4BrFN2S (M+) 245.9304, found 245.9263.

The synthetic route of 1003-98-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nishigaya, Yosuke; Umei, Kentaro; Watanabe, Daisuke; Kohno, Yasushi; Seto, Shigeki; Tetrahedron; vol. 72; 12; (2016); p. 1566 – 1572;,
Bromide – Wikipedia,
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Some common heterocyclic compound, 138526-69-9, name is 1-Bromo-3,4,5-trifluorobenzene, molecular formula is C6H2BrF3, 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: 1-Bromo-3,4,5-trifluorobenzene

Synthesis of diethyl 3,4,5-trifluorophenylphosphonateTrifluorobromobenzene (1.70 mL, 14.2 mmol), diethyl phosphite (2.20 mL, 17.1 mmol), 7V,7V-dicyclohexylmethylamine (4.60 mL, 21.3 mmol) and ethanol (50 mL) were all combined in a nitrogen purged round bottom flask. After stirring for 5 minutes, triphenylphosphine (223 mg, 0.85 mmol) and palladium acetate (64 mg, 0.28 mmol) were added to the flask as one. The solution was heated to 76 0C and allowed to stir overnight. The solution started as a translucent brown color but was clearer by morning. Upon cooling, a silica plug (starting with hexanes as eluent, and increasing the polarity with ethyl acetate as needed) was run and a UV-active spot (Rf = 0.35 in 1:1 hexanes: ethyl acetate) was isolated. The final product is a clear oil (3.477 g, 91 % yield). 1B NMR (400.14 MHz, CDCl3) delta 7.44 (dt, J= 14.4, 6.50 Hz 2H), 4.19 – 4.07 (m, 4H), 1.34 (t, J= 7.07 Hz, 6H). 13C(1H) NMR (100.62 MHz, CDCl3) 5 151.1 (dddd, J= 254.7, 25.4, 10.1, 2.9 Hz, 2C), 142.5 (dtd, J= 258.6, 15.1, 3.3 Hz), 125.0 (dtd, J= 194.5, 5.8, 5.2 Hz), 116.3 – 116 (m, 2C), 62.72 (d, J= 5.63 Hz, 2C), 16.16 (d, J= 6.34 Hz, 2C). 31P(1H) NMR (161.97 MHz, CDCl3): delta 14.94. Analysis calculated (found) %: C 44.79 (44.51), H 4.51 (4.65). MS (FAB, m/z): 283 (M+, 100%). Exact mass calculated (found) for [M+H]+, m/z): 283.07109 (283.07135)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 138526-69-9, its application will become more common.

Reference:
Patent; GEORGIA TECH RESEARCH CORPORATION; IMPERIAL INNOVATIONS Ltd.; HOTCHKISS, Peter; MARDER, Seth; GIORDANO, Anthony; ANTHOPOULOS, Thomas, D.; SOLVAY SA; WO2010/115854; (2010); 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. 54962-75-3, name is 3-Bromo-5-(trifluoromethyl)aniline, A new synthetic method of this compound is introduced below., Application In Synthesis of 3-Bromo-5-(trifluoromethyl)aniline

N2 was bubbled through a solution of 3-bromo-5-trifluoromethyl-phenylamine (2.38 g), 5,5,5′,5′-tetramethyl-[2,2′]bi[[l,3,2]dioxaborinanyl] (2.24g, FrontierScientific) and KOAc (2.92 g), dppf (165 mg, Aldrich) inanhydrous dioxane (50 ml) for 2 min. PdCl2 (dppf) (243 mg,Aldrich) was added and the reaction was heated to 80C for 4h. After cooling to RT, the mix was diluted with 50 mL ofEt20, filtered through Celite, and the filtrate wasconcentrated in vacua. The residue was dissolved in Et20(100 mL) , washed with sat. NaHC03 aqueous solution (50 mL)followed by brine (50 mL). The organic phase was dried overNa2SO4 and concentrated in vacua. The residue wasdissolved in 3:2 Et20/Hex (100 mL) , filtered through Celiteand the filtrate was concentrated in vacua to afford a darkbrown semi-solid.

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; AMGEN INC.; WO2006/12374; (2006); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 129316-09-2,Some common heterocyclic compound, 129316-09-2, name is 1,3-Dibromo-5-(tert-butyl)benzene, molecular formula is C10H12Br2, 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, 33.4 g (0.20 mol) of 3-nitrophenylboronic acid and 29.2 g (0.1 mol) of 3,5-dibromo-tert-butylThe benzene was added to a 1000 ml three-necked flask, and a mixture of 350 ml by volume of 2:1 toluene and ethylene glycol dimethyl ether was added.Solvent, 2.31 g (0.002 mol) of tetrakistriphenylphosphine palladium catalyst and 200 ml of sodium carbonate lye at a concentration of 1 mol / L, room temperatureAfter stirring for half an hour, the temperature was raised to reflux state for 5 hours, and after completion of the reaction, it was filtered, dried and further recrystallized to obtain a mediumThe interstitial compound 3,5-bis(3-nitrophenyl)-tert-butylbenzene has a yield of 91% (the mass of the intermediate compound actually obtained)Obtained from the ratio of the mass of the intermediate compound obtained theoretically).

The synthetic route of 129316-09-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Changzhou University; Wang Chengyi; Yu Bin; Zhao Xiaoyan; Li Jian; Ren Qiang; (6 pag.)CN108358795; (2018); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 7051-34-5, These common heterocyclic compound, 7051-34-5, name is (Bromomethyl)cyclopropane, 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 1 : A mixture of 4-hydroxybenzaldehyde (1.0 g, 8.19 mmol), (bromomethyl)cyclopropane (1.33 g, 9.83 mmol) and K2CO3 (2.26 g, 16.38 mmol) in DMF (10.0 mL, anhydrous) was stirred at 20 C for 12 hours. The solution was diluted with water (20 mL). The aqueous phase was extracted with ethyl acetate (60 mL chi 3). The combined organic phase was washed with brine (20 mL * 1 ), dried over anhydrous Na2SO4 , filtered and concentrated in vacuum. The residue was purified by silica gel chromatography (petroleum ether/ethyl acetate=10/1 , 1/1 ) to give 4-(cyclopropylmethoxy)benzaldehyde (1.3 g, 87% yield).

The synthetic route of 7051-34-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; H. LUNDBECK A/S; KEHLER, Jan; RASMUSSEN, Lars, Kyhn; LANGGARD, Morten; JESSING, Mikkel; VITAL, Paulo, Jorge, Vieira; JUHL, Karsten; (157 pag.)WO2018/78038; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 18648-66-3, name is 2-(4-Bromophenyl)-1,1-diphenylethylene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of 2-(4-Bromophenyl)-1,1-diphenylethylene

For 500 ml three-necked flask was added (2-(4-bromophenyl)ethene-1,1-diyl)dibenzene (10.1g, 30mmol) and 4-aminophenylboronic acid hydrochloride (6.07g, 35mmol). Add 200 ml tetrahydrofuran, stirring to form a uniform clear solution. Add 90 ml K2CO3 solution (2M). Under Ar gas protection, raise temperature to 80 C, rapidly add 0.02g Pd(PPh3)4. Stirring reflux reaction 24h. Cooling to room temperature, separating takes organically phase, the aqueous phase is CH2Cl2Extraction two times, the combined organic phase, adding anhydrous MgSO4Drying. Pumping the filtrate, mixes the silica gel decompression turns on lathe does solvent, in order to CH2Cl2/Normal hexane as eluent for column chromatography, collecting ultraviolet ray, turns on lathe does solvent under reduced pressure, vacuum drying, be pale yellow green powder 9.61g, yield 92%.

The synthetic route of 18648-66-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sun Yat-sen University; Zhang, Yi; Zhou, Zhuxin; Xu, Jiarui; Liu, Siwei; Chi, Zhenguo; (13 pag.)CN106565617; (2017); A;,
Bromide – Wikipedia,
bromide – Wiktionary