Author: Jessica.F

These common heterocyclic compound, 89359-54-6, name is 9-Bromo-1-nonene, 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. SDS of cas: 89359-54-6

10470] To a flame dried 500 mE RB flask, freshly activated Mg turnings (9 g) were added and the flask was equipped with a magnetic stir bar, an addition thnnel and a reflux condenser. This set-up was degassed and flushed with argon and 100 mE of anhydrous ether was added to the flask via syringe. The bromide 3 (51.3 g, 250 mmol) was dissolved in anhydrous ether (100 mE) and added to the addition thnnel. About 5 mE of this ether solution was added to the Mg turnings while stirring vigorously. An exothermic reaction was noticed (to confirmlaccelerate the Grignard reagent formation, 5 mg of iodine was added and immediate decolorization was observed confirming the formation of the Grignard reagent) and the ether started refluxing. The rest of the solution of the bromide was added dropwise while keeping the reaction under gentle reflux by cooling the flask in watet Afier the completion of the addition the reaction mixture was kept at 35C. for 1 hour and then cooled in ice bath. Ethyl formate (9 g, 121 mmol) was dissolved in anhydrous ether (100 mE) and transferred to the addition thnnel and added dropwise to the reaction mixture with stirring. An exothermic reaction was observed and the reaction mixture started refluxing. After the initiation of the reaction the rest of the ethereal solution of formate was quickly added as a stream and the reaction mixture was stirred for a further period of 1 h at ambient temperature. The reaction was quenched by adding 10 mE of acetone dropwise followed by ice cold water (60 mE). The reaction mixture was treated with aq. H2S04 (10% by volume, 300 mE) until the solution became homogeneous and the layers were separated. The aq. phase was extracted with ether (2×200 mE). The combined ether layers were dried (Na2 SO4) and concentrated to afford the crude product which was purified by colunm (silica gel, 0-10% ether in hexanes) chromatography. The product fractions were evaporated to provide the pure product 11 as a white solid (30.6 g, 90%). ?H NMR (400 MHz, CDC13) oe 7.26 (s, 1H), 5.81 (ddt, J=16.9, 10.2, 6.7 Hz, 8H), 5.04-4.88 (m, 16H), 3.57 (dd, J=7.6, 3.3 Hz, 4H), 2.04 (q, J=6.9 Hz, 16H), 1.59(s, 1H), 1.45 (d,J=7.5 Hz, 8H), 1.43-1.12 (m, 94H), 0.88 (t, J=6.8 Hz, 2H). ?3C NMR (101 MHz, cdcl3) oe 139.40, 114.33, 77.54, 77.22, 76.90, 72.21,37.70,34.00,29.86,29.67,29.29,29.12,25.85.

The synthetic route of 9-Bromo-1-nonene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALNYLAM PHARMACEUTICALS, INC.; MANOHARAN, Muthiah; MAIER, Martin; JAYARAMAN, Muthusamy; MATSUDA, Shigeo; NAIR, Jayaprakash K.; RAJEEV, Kallanthottathil G.; AKINC, Akin; BAILLIE, Thomas A.; (104 pag.)US2016/9637; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

61613-22-7, name is 2-Bromo-N-phenylaniline, 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. Computed Properties of C12H10BrN

After dissolving 10 g of 2-bromo-N-phenylphenylamine in 100 ml of tetrahydrofuran, the reaction temperature was lowered to -78 C,Slowly add 20 ml of 2.5 M butyllithium and stir for 1 h. 11 g of benzophenone was dissolved in 100 ml of tetrahydrofuran and slowlyAfter dropping, the temperature was increased to room temperature and stirred for 12 h. After the reaction has ended, distilled water and methylene chloride will be usedRow extraction and drying by anhydrous magnesium sulfate followed by filtration under reduced pressure gave the solid which was dissolved in 100 ml of acetic acid, 7 ml of sulfuric acid was added dropwise and the mixture was reflux-stirred. After the reaction was completed, the mixture was extracted with distilled water and methylene chlorideThe resulting solid was purified by column chromatography to give Intermediate B-1 (7.1 g, yield 53%).

The synthetic route of 61613-22-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Changchun Hai Purunsi Technology Co., Ltd.; Liu Xiqing; Cai Hui; (24 pag.)CN107400085; (2017); A;,
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. 10485-09-3, name is 2-Bromoindene, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 10485-09-3

A Schlenk flask was charged with a magnetic stir bar and Mg turnings (264 mg, 1 1 mmol, 6.7 eq.) and flame-dried under vacuum. After cooling, the flask was purged to N2, anhydrous THF (3 mL) was added to just cover the turnings, and stirring was commenced. Several drops of 1 ,2-dibromoethane was added as initiator, and a heat gun used to briefly reflux the contents, after which the flask was placed in a 25 C water bath. In a separate flame-dried flask under N2 atmosphere, 2-bromoindene (715 mg, 3.67 mmol, 2.2 eq.) was dissolved in 10 mL anhydrous THF. A cannula was then used to transfer this solution onto the activated magnesium turnings over 5 min, resulting in a red, opaque solution. After 1 .5 h, a separate flame-dried flask under N2 atmosphere was charged with ‘Pr2NBCI2(0.3 g, 1.65 mmol, 1 .0 eq.) in 10 mL anhydrous THF and cooled to -78C. To this was added, by cannula, the Grignard solution over 10 min., and the reaction flask was brought to ambient temperature for overnight. The pale orange solution was concentrated and the residue was dissolved in CH2CI2 (30 mL). The suspension was filtered through celite and the filtrate was concentrated to provide compound 1 1 (0.56 g, quant.) as a yellow powder.11B NMR (128 MHz, CD2CI2) delta 40.4;1H-NMR (400 MHz, CD2CI2) 7.37 (2H, d, J = 7.6 Hz), 7.33 (2H, d, J = 7.6 Hz), 7.19 (2H, t, J = 7.6 Hz), 7.06 (2H, td, J = 7.6, 1.2 Hz), 6.81 (2H, s), 3.85 (2H, m), 3.38 (4H, s), 1.25 (12H, d, J = 6.8 Hz).

According to the analysis of related databases, 10485-09-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SABIC GLOBAL TECHNOLOGIES B.V.; AL-SHAMMARI, Haif; SUN, Yunshan; STEPHAN, Douglas; AL HUBISH, Salah; JIANGTAO, Zhu; (36 pag.)WO2016/37960; (2016); 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. 50548-45-3, name is 1-Bromodibenzo[b,d]furan belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C12H7BrO

20 g (80 mmol) of dibenzofuran-1-boronic acid, 2.06 g(40.1 mmol) of iodine, 3.13 g (17.8 mmol) of periodic acid, 80 ml of aceticacid, 5 ml of sulfuric acid, 5 ml water and 2 ml chloroform were stirred at 65C for 3 h. After cooling, water was added to the mixture, and the precipitatedsolids were filtered off with suction, and washed three times with water. Thenthe product was recrystallized from dichloromethane / heptane. The yield is25.6 g (68 mmol), equivalent to 85% of theory.

The synthetic route of 50548-45-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Patent GMBH; Faram, Amir Hossain; Yatsi, Anya; Evemilley, Thomas; Grossman, Tobias; Krevor, Jonas Valentine; Tobelmann, Laruese; (100 pag.)KR2016/28524; (2016); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 176317-02-5, A common heterocyclic compound, 176317-02-5, name is 1-Bromo-2,3,4-trifluorobenzene, molecular formula is C6H2BrF3, 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: 5-bromo-2,3,4-trifluorobenzoic acid To a solution of 1-bromo-2,3,4-trifluorobenzene (13.64 g, 64.6 mmol) in THF (120 mL) was added lithium diisopropylamide (2.0 M in THF, 33.9 mL, 67.8 mmol) at -78 C. under nitrogen atmosphere. After stirring for 1 h at -78 C., the mixture was transferred to a bottle with dry ice. The mixture was stirred overnight at room temperature. The reaction was quenched with 10% aqueous HCl (300 mL) and extracted with ethyl acetate (200 mL*3). The combined organic extracts were washed with 5% sodium hydroxide (300 mL). The aqueous layer was acidized to pH 1 and extracted with ethyl acetate (200 mL*3). The combined organic extract was dried over Na2SO4, filtered and concentrated under reduced pressure to afford the desired product (white solid, 13.51 g, 82% yield). 1H NMR (400 MHz, CDCl3): delta 13.94 (s, 1H), 7.95 (m, 1H).

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; TIANJIN BINJIANG PHARMA, INC.; Tian, Hongqi; Ji, Conghui; Liu, Chunlei; Kong, Li; Cheng, Ying; Huang, Gongchao; US2014/371278; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 6320-40-7, These common heterocyclic compound, 6320-40-7, name is 1,3,5-Tribromo-2-methylbenzene, 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.

Synthesizing of Intermediates A and B 3.3g (10 mmol) of 2,4,6-tribromotoluene was dissolved in 30 mL of diethylether. The resulting solution was cooled to -78 C and 4.4mL (11 mmol) of normalbutylithium (2.5M in Hexane) was slowly added thereto. The resulting solution was stirred at -78C for one hour and 1.48g (11 mmol) of cooper chloride (II) was added thereto at -78C. The reactant product was stirred for 5 hours and cleaned using distilled water and ethylacetate at room temperature. The cleaned ethylacetate layer was dried over MgSO4 and dried under a reduced pressure, thereby producing a crude-product. The pre-product was refined through a column chromatography and the refined result was recrylstallized in dichloromethane and hexane, thereby producing white solid intermediates A and B. Amounts of A and B were 622 mg (yield 25%) and 746 mg (yield: 30%), respectively. Intermediate A : 1H NMR (CDCl3, 400MHz) delta (ppm) 7.74 (d, 4H), 7.18 (d, 4H), 2.06 (s, 6H); 13C NMR (CDCl3, 100MHz) delta (ppm) 142.8, 134.9, 134.5, 131.1, 126.4, 119.4, 19.9 Intermediate B : 1H NMR (CDCl3, 400MHz) delta (ppm) 7.60 (s, 4H), 2.61 (s, 6H); 13C NMR (CDCl3, 100MHz) delta (ppm) 138.3, 137.2, 129,9, 125.8, 23.5

The synthetic route of 6320-40-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Samsung SDI Co., Ltd.; EP1752442; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 69038-76-2, name is 4-Bromo-N1-methylbenzene-1,2-diamine, 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 69038-76-2, HPLC of Formula: C7H9BrN2

After methyl dichloro(methoxy)acetate (2.5 ml) was added to a solution of 4-bromo-N1-methylbenzene-1,2-diamine (1.0 g), N,N-diisopropylethylamine (7.1 ml) in 1,2-dichloroethane (30 ml), the reaction mixture was stirred at room temperature for 1 hour, and then stirred at 60 C. for 3 days. After the reaction mixture was cooled to room temperature, a saturated aqueous sodium hydrogen carbonate solution was added thereto, and extraction was carried out using chloroform. After the organic layer was dried over anhydrous sodium sulfate, the desiccant was removed, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate), thereby obtaining methyl 5-bromo-1-methyl-1H-benzimidazole-2-carboxylate (820 mg) as a solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-N1-methylbenzene-1,2-diamine, and friends who are interested can also refer to it.

Reference:
Patent; ASTELLAS PHARMA INC.; Ohnuki, Kei; Azami, Hidenori; Sawada, Yuki; Shin, Takashi; Kuramoto, Kazuyuki; Kikuchi, Shigetoshi; Saito, Tomoyuki; Hamaguchi, Hisao; Nagashima, Takeyuki; US2015/266869; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 1435-53-6, name is 2,4-Dibromo-1-fluorobenzene, 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. Application In Synthesis of 2,4-Dibromo-1-fluorobenzene

1,3-Dibromo-4-fluorobenzene (837 mg) was dissolved in a toluene-THF (10:1) mixture (15 ml). The mixture was cooled to -78 C. and n-butyllithium (2.64 M, 1.19 ml) was added dropwise. After stirring at the same temperature for one hour, a solution of (+/-)-3,3a,4,5-tetrahydro-7H-pyrano[3,4-c]isoxazole obtained in Preparation Example 1-(2) (200 mg) in toluene-THF (10:1) (5.0 ml) and a boron trifluoride-diethyl ether complex (394 mul) were added dropwise at the same time. After stirring at the same temperature for three hours, the reaction was terminated with an ammonium chloride solution. The aqueous layer was extracted with ethyl acetate, and the organic layer was washed with water and brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (365 mg).

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

Reference:
Patent; EISAI R&D MANAGEMENT CO., LTD.; US2010/93999; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 827-08-7, name is 1,2-Dibromo-3,4,5,6-tetrafluorobenzene, 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 827-08-7, name: 1,2-Dibromo-3,4,5,6-tetrafluorobenzene

By the following method,A compound represented by the formula (1m) (1,2-bis (2-methyl-5-phenyl-3-thienyl) tetrafluorobenzene) was synthesized.3-Bromo-2-methyl-5-phenylthiophene in a three-necked flask under an argon atmosphere [Literature Description: M.M. Irie, T .; Lifka, S .; Kobatake, N .; Kato, J .; Am. Chem. Soc. , 122, 4871-4876 (2000)] 520 mg (2.1 mmol) was added and dissolved in 15 mL of anhydrous tetrahydrofuran (THF).. After cooling to -78 C., 1.3 mL (2.2 mmol) of 1.6 M n-butyllithium hexane solution was slowly added dropwise. After stirring for 2 hours,Tributyl borate 1.0 mL (3.7 mmol) was slowly added dropwise and stirred for 2 hours.Then return to room temperature,Quenched with water.The mixture was acidified with dilute hydrochloric acid and extracted with diethyl ether.Add sodium hydroxide aqueous solution to the organic layer,After basifying, extraction with diethyl ether was performed again.Add concentrated hydrochloric acid to the aqueous phase,The resulting white precipitate was obtained by filtration. It was dissolved in THF, 120 mg (0.40 mmol) of 1,2-dibromotetrafluorobenzene,2 mL of 20 wt% aqueous sodium carbonate solution and 50 mg (0.043 mmol) of Pd (PPh3) 4 were added and refluxed for 8 hours. The mixture was neutralized with dilute hydrochloric acid, extracted with diethyl ether, salted out, and dried over magnesium sulfate. The solvent was distilled off and the residue was purified by silica gel column chromatography using hexane as a developing solvent.Yield 81 mg, 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; Osaka City University; Kobatake, Seiya; Kitagawa, Daichi; (28 pag.)JP2019/151596; (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. 40422-70-6, name is 1-Bromo-3-(2-bromoethyl)benzene, A new synthetic method of this compound is introduced below., Computed Properties of C8H8Br2

A mixture of 2,4,6-trimethyl-N-((3′-(methylsulfonyl)-[l, r-biphenyl]-4- yl)methyl)benzenesulfonamide (0.443 g, 1 mmol), K2CO3 (0.276 g, 2 mmol), and l-bromo-3-(2-bromoethyl)benzene (0.792 g, 3 mmol) in anhydrous acetonitrile (5 ml) was heated to 85 C for 2 h under microwave irradiation. The white powder was filtered off, the solvent was evaporated and the mixture was dissolved in ethyl acetate and extracted with brine. The organic phase was separated, dried over anhydrous MgS04, filtered and concentrated in vacuo. The remaining crude residue was purified by flash chromatography on silica gel (ethyl acetate/hexanes) to obtain the title compound as white sharp needles (88% based on recovery of the starting materials); FontWeight=”Bold” FontSize=”10″ H NMR (400 MHz, Chloroform-Patent; THE SCRIPPS RESEARCH INSTITUTE; KAMENECKA, Theodore, Mark; BURRIS, Thomas; WO2014/85453; (2014); A2;,
Bromide – Wikipedia,
bromide – Wiktionary