Month: June 2021

Related Products of 21524-34-5, 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 21524-34-5 as follows.

EXAMPLE TEN: Synthesis of Ligand 7; An oven-dried three-neck 250 mL round bottom flask, which was equipped with a magnetic stir bar and charged with magnesium shavings (559 mg, 24.3 mmol), was fitted with a reflux condenser, addition funnel, and glass stopper. The flask was purged with argon and then THF (15 mL) and 2,4,6-triisopropylbromobenzene (2.83 g, 10 mmol) were added via syringe. The reaction mixture was heated to reflux and 1 ,2-dibromethane (40 uL) was added via syringe. The reaction was allowed to stir at reflux for 1 h and then the addition funnel, which was charged with l,2-dibromo-3,4,5,6-tetramethylbenzene (2.92 g, 10 mmol) in 40 mL of THF, was opened and the solution was added over a 1 h period. The mixture was stirred for 5 h at reflux and then cooled to room temperature where CuCl (1.0 g, 10 mmol) was added quickly to the reaction mixture. Next, ClPCy2 (2.65 mL, 10 mmol) was then added in a dropwise fashion and the reaction mixture was heated to 75 0C for 60 h. The reaction mixture was then cooled to room temperature, diluted with EtOAc, washed 3 times with 30% NH4OH, dried over MgSO4, and concentrated under reduced pressure. The crude material was recrystallized from benzene to yield the product as a white solid (1.507 g, 28% yield). 1H NMR (300 MHz, CDCl3) delta: 7.36 (s, 5H), 7.15 (s, 2H), 2.99 (septet, J= 7.0 Hz, IH), 2.44 (s, 3H), 2.35-2.14 (m, HH), 1.98 (s, 2H), 1.80-1.44 (m, 14H), 1.39-1.04 (m, 22H), 0.91 (d, J= 6.5 Hz, 6H) ppm. 13C NMR (75 MHz, CDCl3) delta: 150.9, 145.8, 145.4, 144.6, 140.0, 138.5, 135.8, 135.6, 135.5, 135.5, 128.6, 124.3, 40.2, 39.9, 35.4, 35.2, 34.5, 30.7, 29.5, 27.8, 27.7, 27.4, 27.2, 25.9, 25.0, 24.6, 21.2, 20.8, 17.7, 17.3 ppm (Observed complexity is due to P-C splitting). 31P NMR (121 MHz, CDCl3) delta: 16.33 ppm.

According to the analysis of related databases, 21524-34-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MASSACHUSETTS INSTITUTE OF TECHNOLOGY; WO2009/76622; (2009); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 43204-63-3, A common heterocyclic compound, 43204-63-3, name is Bis(2-Bromoethyl)amine hydrobromide, molecular formula is C4H10Br3N, 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.

Add 5-amino-3,4-dihydroquinolin-2(1H)one 7 (5.00 g, 30.83 mmol) to 40 ml of water in turn, di-(2-bromoethyl)amine hydrobromide (50.57 g, 33.91 mmol), stirring to 80 C, An aqueous solution of potassium hydroxide (1.90 g, 33.91 mmol, 10 ml) was added dropwise in three portions over half an hour. After the addition is completed, the reaction is heated to 100 C. The reaction was further incubated for 3 hours. After completion of the reaction, the mixture was cooled to room temperature, filtered, and the filtrate was adjusted to pH 10 with a 10% aqueous potassium hydroxide solution to precipitate a large white solid. Filtered, washed with a suitable amount of water, dried to give a white powdery solid 8 (6.4 g, yield 61%, Mp 235-237 C);

The synthetic route of 43204-63-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Southwest University; Ji Qinggang; Deng Qiao; (15 pag.)CN109438344; (2019); A;,
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 185122-74-1 as follows. Computed Properties of C9H10BrN

At 0 0C and under protective atmosphere, a solution of 2-Propanesulfonyl chloride (1 1.87 ml_, 121 mmol) in DCM (121 ml.) was added gradually to a solution of 5-bromo-2,3- dihydro-1 H-inden-1 -amine (12.8 g, 60.4 mmol) and 1 ,8-Diazabicyclo[5.4.0]undec-7-ene (4.83 ml_, 32.1 mmol) in Dichloromethane (300 ml_). The reaction was stirred at rt overnight. The reaction mixture was washed with 1 N KHSO4 (1x) and sat NaHCObeta (2x) before being dried on Na2SO4 and solvent evaporated in vacuo to afford a green oil. Purification by column chromatography (25% EtOAc in heptane) afforded the title compound as a white solid.(6.0 g, 31 %). MS (ESI) : m/z [M – H]” 317.0

According to the analysis of related databases, 185122-74-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; N.V. Organon; GILLEN, Kevin James; GILLESPIE, Jonathan; JAMIESON, Craig; MACLEAN, John Kinnaird Ferguson; MOIR, Elizabeth Margaret; RANKOVIC, Zoran; WO2010/115952; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 327-52-6, A common heterocyclic compound, 327-52-6, name is 1-Bromo-2,4,5-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.

[0141] Into a 100 mL three- necked flask were added 4.62 g 1- bromo- 2, 4, 5- trifluorobenzene (0.022 mol) andanhydrous tetrahydrofuran (50 mL) . The resulting mixture was cooled to- 20 C. The solution of isopropylmagnesiumbromide (22 mmol) in tetrahydrofuran (22 ml, 1 M THF) was slowly added dropwise under nitrogen. After the additionwas complete, the reactants were maintained at- 20 C for later use.[0142] Cuprous bromide – dimethyl sulfide (0.41 g, 0.002 mol) was suspended in 5 ml anhydrous tetrahydrofuran. Theresulting mixture was cooled to -5 C. The Grignard reagent as described above was slowly added dropwise undernitrogen. After 15 min, a solution of the acridine compound as shown in the above reaction formula (2.81 g, 0.015 mol)in 30 mL tetrahydrofuran was slowly added dropwise. After additional 5 min, 50 mL saturated solution of ammoniachloride was added to quench the reaction. Into this obtained solution was added 50 mL ethyl acetate. The separatedwater layer was extracted with another 50 mL ethyl acetate. The obtained organic layers were collected together andfurther washed with saturated solution of sodium chloride and then dried over anhydrous sodium sulfate, followed byfiltration and concentration to obtain a crude product, which was further treated by column chromatography to obtain acompound (3.69 g, 0.0115 mol, yield 77%).1H NMR (500 MHz, CDCl3) delta 7.05 (d, J = 8.3 Hz, 1 H), 6.91 (d, J = 6.6 Hz, 1 H), 4.56 (d, J = 9.0 Hz, 1H), 4.13?3.96 (m,1 H), 3.68 (d, J = 6.0 Hz, 2H), 2.85?2.65 (m, 2H), 1.86 (dd, J = 12.4, 7.7 Hz, 1H), 1.68 (s, 1H), 1.42 (s, 9H). Ms (M++1): 320.

The synthetic route of 327-52-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhejiang Hisoar Pharmaceutical Co., Ltd; PAN, Xianhua; LI, Weijin; ZHANG, Qunhui; RUAN, Libo; YU, Wansheng; DENG, Fei; MA, Tianhua; HUANG, Mingwang; HE, Minhuan; EP2647624; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 55289-36-6,Some common heterocyclic compound, 55289-36-6, name is 3-Bromo-2-methylaniline, molecular formula is C7H8BrN, 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 atmosphere, 3-bromo-2-methylaniline (5.01g, 26.9 mmol) was dissolved in DCM (100 mL). To this solution, cooled with ice bath, TEA (7.5 mL, 53.9 mmol) and 4-tert-butylbenzoyl chloride (5.3 g, 26.9 mmol) were added dropwise and stirred at 0 C for 4 h. The reaction mixture was diluted with DCM (100 mL), washed with water (2×30 mL), 1N hydrochloric acid solution (30 mL), saturated sodium hydrogen carbonate solution (30 mL) and brine (30 mL), then the organic layer was dried over sodium sulfate, filtered and concentrated. The crude material was suspended in hexane, then the precipitate was collected by filtration, washed with hexane then dried to afford N-(3-bromo-2-methylphenyl)-4-(tert-butyl)benzamide (9.0 g). 1H NMR (400 MHz, DMSO-d6) delta 10.06 (s, 1H), 7.92 (d, J = 8.4 Hz, 2H), 7.54 (m, 3H), 7.33 (d, J = 7.7 Hz, 1H), 7.18 (t, J = 8.0 Hz, 1H), 2.27 (s, 3H), 1.32 (s, 9H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Bromo-2-methylaniline, its application will become more common.

Reference:
Patent; Carna Biosciences, Inc.; KAWAHATA, Wataru; ASAMI, Tokiko; SAWA, Masaaki; ASAMITSU, Yuko; IRIE, Takayuki; MIYAKE, Takahiro; KIYOI, Takao; EP2824099; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 52723-82-7, These common heterocyclic compound, 52723-82-7, name is 4-Bromo-5-fluoro-2-methylaniline, 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.

A solution of 4-bromo-5-fluoro-2-methylaniline (10.2 g, 50 mmol) and 3- chlorobenzenecarboperoxoic acid (34.5 g, 200 mmol) in DCE (10 mL) was stirred under nitrogen at reflux for 2 hours. After cooling to rt, the mixture was dispersed between DCM and saturated aqueous Na2S03 solution. The organic layer was collected, concentrated to dryness and purified by flash column chromatography to give the title compound as a brown oil (7.02 g, 60.0percent yield).

The synthetic route of 52723-82-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; ARORA, Nidhi; BACANI, Genesis M.; BARBAY, Joseph Kent; BEMBENEK, Scott D.; CAI, Min; CHEN, Wei; DECKHUT, Charlotte Pooley; EDWARDS, James P.; GHOSH, Brahmananda; HAO, Baoyu; KREUTTER, Kevin; LI, Gang; TICHENOR, Mark S.; VENABLE, Jennifer D.; WEI, Jianmei; WIENER, John J. M.; WU, Yao; ZHU, Yaoping; ZHANG, Feihuang; ZHANG, Zheng; XIAO, Kun; (1000 pag.)WO2017/100668; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 6274-57-3, A common heterocyclic compound, 6274-57-3, name is 1-(4-Bromophenyl)-N,N-dimethylmethanamine, molecular formula is C9H12BrN, 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: Pd(PPh3)4 (3 mol%) was added to a suspension of the appropriate benzoxazole 7 and (het)aryl bromide (1 equiv) in 1 M aq K2CO3 (3equiv) and 1,4-dioxane (0.15 M) at r.t. The mixture was stirred at reflux for 2 h then cooled to r.t. H2O was added, and the mixture was extracted with EtOAc. The organic layers were combined, washed with brine, dried (NaSO4), filtered, and concentrated in vacuo. The residue was purified by column chromatography (silica gel,hexane-EtOAc or CHCl3-MeOH).

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; Fukaya, Takayuki; Masumoto, Shuji; Synthesis; vol. 45; 23; (2013); p. 3269 – 3275;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 118527-30-3, name is 2-Bromo-1,3-bis(trifluoromethyl)benzene, 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 118527-30-3, Application In Synthesis of 2-Bromo-1,3-bis(trifluoromethyl)benzene

General procedure: 12.6 g (38.32 mmol) of 9H-[3,9?]bicarbazolyl [18628-07-4], 7 g (38.32 mmol) of 2-bromo-1,3-ditrifluoromethylbenzene [118527-30-3] and 16 g of K2CO3are suspended in 300 mL of p-xylene. To the suspension are added 0.86 g (3.84 mmol) of Pd(OAc)2and 7.6 mL of a 1M tri-tert-butylphosphine solution. The reaction mixture is heated under reflux for 16 h. After cooling, the organic phase is removed, washed three times with 200 mL of water and then concentrated to dryness. The residue is subjected to hot extraction with toluene, recrystallized from toluene and finally sublimed under high vacuum. Yield: 14.5 g (35 mmol), 87% of theory; purity 99.9%

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; MerckPatent GMBH; Suttessel, Philip; Faram, AmirHossain; Blume, Christoph; Yatzi, Anya; (85 pag.)KR2015/132872; (2015); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 24358-62-1, A common heterocyclic compound, 24358-62-1, name is 1-(4-Bromophenyl)ethylamine, molecular formula is C8H10BrN, 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.

In addition to the foregoing, numerous other chromatographic separations using a column bonded with a CSP including a derivatized cyclofructan residue were carried out. Tables 5-9 list some additional examples of chromatographic separations using a column bonded with a CSP of the present invention. AU examples of chromatographic separations using columns bonded with CSPs of the present invention were carried out using the following experimental conditions and procedures.|0132| The high performance liquid chromatography (HPLC) column packing system was composed of an air driven fluid pump (HASKEL, DSTV- 122), an air compressor, a pressure regulator, a low pressure gauge, two high-pressure gauges (10,000 and 6,000 psi), a slurry chamber, check valves, and tubings. The CSPs were slurry packed into a 25 cm x 0.46 cm (inner diameter, I. D.) stainless steel column.|0133| The HPLC system was an Agilent 1 100 system (Agilent Technologies, Palo Alto,CA), which consisted of a diode array detector, an autosampler, a binary pump, a temperature- controlled column chamber, and Chemstation software. All chiral analytes were dissolved in ethanol, methanol, or other appropriate mobile phases, as indicated. For the LC analysis, the injection volume and flow rate were 5 muL and 1 mL/min, respectively. Separations were carried out at room temperature (~20 0C) if not specified otherwise. The wavelengths of UV detection were 195, 200, 210, and 254 nm. The mobile phase was degassed by ultrasonication under vacuum for 5 min. Each sample was analyzed in duplicate. Three operation modes (the normal phase mode, polar organic mode, and reversed phase mode) were tested, unless indicated otherwise. In the normal phase mode, heptane with ethanol or isopropanol was used as the mobile phase. In some cases, trifluoroacetic acid (TFA) was used as an additive, as indicated. The mobile phase of the polar organic mode was composed of acetonitrile/methanol and small amounts of acetic acid and triethylamine. Water/acetonitrile or acetonitrile/acetate buffer (20 mM, pH = 4.1 ) was used as the mobile phase in the reversed-phase mode.|0134| Two different supercritical fluid chromatographic instruments were used. One was a Berger SFC unit with an FCM 1200 flow control module, a TCM 2100 thermal column module, a dual pump control module, and a column selection valve. The flow rate was 4 mL/min. The cosolvent was composed of methanol/ethanol/isopropanol = 1 : 1 : 1 and 0.2% diethylamine (DEA). The gradient mobile phase composition was 5% cosolvent hold during 0- 0.6 min, 5-60% during 0.6-4.3 min, 60% hold during 4.3-6.3 min, 60%-5% during 6.3-6.9 min, and 5% hold during 6.9-8.0 min. The other SFC system was a Jasco (MD, USA) system comprised of an autosampler unit (AS-2059-SF Plus), a dual pump module (PU-2086 Plus), a column thermostat module (CO-2060 Plus), a UV/Vis detector (UV-2075 Plus), and a back pressure regulator module (SCH-Vch-BP). Unless otherwise specified, the mobile phase was composed of CCVmethanol (0.1 % TFA or 0.1% diethylamine). The flow rate was 3 mL/min.|0135| For the calculations of chromatographic data, the “dead time” to was determined by the peak of the refractive index change due to the sample solvent or determined by injecting l ,3,5-tri-/e/-/-butylbenzene in the normal phase mode.

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; BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM; ARMSTRONG, Daniel, W.; PING, Sun; BREITBACH, Zachary, S.; WANG, Chunlei; WO2010/148191; (2010); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 201138-91-2,Some common heterocyclic compound, 201138-91-2, name is 4,6-Dibromodibenzo[b,d]furan, molecular formula is C12H6Br2O, 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.

13.4 g phenyl boric acid and 32.6 g 4,6-dibromo-dibenzofuran were added into a 2 L three-neck flask, followed by adding 700 mL toluene and 150 mL ethanol to dissolve. The reaction mixture was aerated with nitrogen gas for 15 minutes, then 150 mL aqueous K2CO3 solution (6.0 eq., 2M) and 2.3 g Pd(PPh3)4 (2 mol %) were sequentially added. The reaction mixture was heated up to 110 C. and reacted overnight. After the reaction finished, the residual was absorbed by the added activated carbon, filtered by suction filtration and removed with solvent by rotary evaporation, then followed by drying and recrystallization with a mixture of toluene and ethanol, to produce 28.1 g Intermediate (11) at a yield of 87%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4,6-Dibromodibenzo[b,d]furan, its application will become more common.

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