Month: May 2021

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. 17247-58-4, name is (Bromomethyl)cyclobutane belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: (Bromomethyl)cyclobutane

A stirred solution of the ketimime 1a’ (50 g, 187.1 mmol, available from Aldrich Chemical Company, Milwaukee, Wis.) under N2 in dry THF (400 mL) was cooled to -78 C. and treated with 1 M solution of K-tBuO (220 mL, 1.15 equiv.) in THF. The reaction mixture was warmed to 0 C. and stirred for 1 h and treated with bromomethylcyclobutane (28 mL, 249 mmol). The reaction mixture was stirred at room temperature for 48 h and concentrated in vacuo. The residue was dissolved in Et2O (300 mL) and treated with aq. HCl (2 M, 300 mL) The resulting solution was stirred at room temperature for 5 h and extracted with Et2O (1 L). The aqueous layer was made basic to pH12-14 with aq. NaOH (50%) and extracted with CH2Cl2 (3×300 mL). The combined organic layers were dried (MgSO4), filtered, and concentrated to give pure amine (1b’, 18 g) as a colorless oil.

The synthetic route of 17247-58-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Schering Corporation; US2006/276406; (2006); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 2695-48-9, name is 8-Bromo-1-octene, 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 2695-48-9, Formula: C8H15Br

Intermediate 104b tert-butyl 4-hydroxydodec-11-enoate Magnesium turnings (307 mg, 12.64 mmol) was weighed into a pre-dried flask and dried in an oven at 120 C for 2 hours. The flask was removed from the oven, sealed, and cooled to ambient temperature. To the flask, 6 ml_ of anhydrous THF and one particle of iodine was added, followed by addition of 8-bromooct-1-ene (1.570 g, 8.22 mmol). A condenser was added to the flask, and the whole system was exhanged with N2 and protected under N2 ballon. The reaction was heated with a heating until the brown color from the iodine disipated. The reaction was heated at reflux until most of magnesium was consumed (about 1.5 hr), then cooled to room temperature. To a solution of Intermediate 104a (1.0g, 6.32mmol) in 25ml THF cooled in a dry-ice acetone bath, the freshly prepared Grignard reagent was added dropwise. The reaction was stirred for 1 h, then warmed to ambient temperature. The reaction was quenched with sat. aq. NaHC03, and extracted with ethyl acetate. The combined organics were dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure and purfied on silica gel with 10% ethyl acetate / heptane to afford the desired product (890mg, 60%). 1H NMR (400 MHz, CDCI3) delta = 5.61-5.85 (m, 1 H), 4.80-4.98 (m, 2H), 3.48-3.62 (m, 1 H), 2.26-2.36 (t, J=7.5Hz, 2H), 1.50- 1.78 (m, 4H), 1.35-1.44 (m, 19H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 8-Bromo-1-octene, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; BRITO, Luis; CHEN, Delai; GAMBER, Gabriel Grant; GEALL, Andrew; LOVE, Kevin; ZABAWA, Thomas; ZECRI, Frederic; WO2015/95346; (2015); 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., COA of Formula: C7H5BrF3N

INTERMEDIATE 13 -( 1 H- 1 ,2,4-Triazol- 1 -yl)-5-(trifluoromethyl)aniline[00146] 3-Bromo-5-(trifluoromethyl)aniline (3.5 g, 14.6 mmol), copper(I) iodide (1.39g, 7.3 mmol), potassium carbonate (6.0 g, 43.7 mmol) and lH-l,2,4-triazole (3.0 g, 43.7 mmol) in NMP (10 mL) were heated at 195 0C for 2 hours. The reaction mixture was filtered through a plug of silica gel, washed with ethyl acetate, and concentrated. The crude residue was purified by silica gel column chromatography (stepwise gradient, from hexanes to 75% ethyl acetate/hexanes). The fractions were concentrated, dissolved in diethyl ether (150 mL), washed with water (4 x 50 mL), dried over Na2SO4, filtered and concentrated to afford Intermediate 1 (1.95 g, 58.6 % yield) as a tan solid. HPLC: Rt = 1.193 min. (PHENOMENEX Luna 5 micron C18 4.6 x 30 mm, 10-90% aqueous methanol containing 0.1% TFA, 2 min. gradient, flow rate = 5 mL/min., detection at 254 nm). MS (ES): m/z = 229.01 [M+H]+. 1H NMR (500 MHz, DMSOd6) delta ppm 8.27 (1 H, s), 7.34 (1 H, s), 6.47 (2 H, d, J = 2.29), 6.14 (1 H, s). Intermediate 1 was used in the synthesis of Examples 13, 104, 165, 169, and175.

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; BRISTOL-MYERS SQUIBB COMPANY; FINK, Brian; CHEN, Libing; GAVAI, Ashvinikumar; HE, Liqi; KIM, Soong-Hoon; NATION, Andrew; ZHAO, Yufen; ZHANG, Litai; WO2010/42699; (2010); 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. 586-61-8, name is 1-Bromo-4-isopropylbenzene, This compound has unique chemical properties. The synthetic route is as follows., name: 1-Bromo-4-isopropylbenzene

Compound 1-3 (5.28 g, 10 mmol) and 4-isopropyl-bromobenzene (4 g, 20 mmol)Add in a three-necked flask and stir to dissolve with 100 ml of anhydrous toluene.Nitrogen protection followed by Pd(dba)2 (575mg, 1mmol)And sodium tert-butoxide (1.93 g, 20 mmol),Then, a solution of 10% of tri-tert-butylphosphine toluene (4.5 ml) was added, and the reaction solution was stirred and refluxed overnight.After the reaction was completed, it was cooled, and the reaction liquid was washed three times with 100 ml of water.The organic phase was dried over anhydrous sodium sulfate and then evaporated to remove solvent.The residue was purified by DCM/PE (1:15).Obtained white solid compound Cl(4.95 g, yield 56%).

According to the analysis of related databases, 586-61-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Guangzhou Huarui Optoelectric Materials Co., Ltd.; Yang Xi; Pan Junyou; Chen Jia; (38 pag.)CN109608342; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 22385-77-9,Some common heterocyclic compound, 22385-77-9, name is 1-Bromo-3,5-di-tert-butylbenzene, 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.

The reaction flask was sequentially charged with raw materials la (56 mg, 0.2 mmol) and 21 (1 mL), cesium carbonate (130 mg, 2.0 eq), dilute ligand L2-1 (2.6 mg, 5 molpercent), tricyclohexylphosphine tetrafluoroboron Acid salt (1.8 mg, 2.5 molpercent), [Rh (cod) Cl] 2 (2.5 mg, 2.5 molpercent), di-tert-butylphosphonium chloride (18 mg, 0.1 mmol) and toluene (2 mL) in nitrogen In an atmosphere, the mixture was stirred at 120 ° C for 24 hours, cooled to room temperature, diluted with ethyl acetate (5 mL), diluted with EtOAc (2 mL), and brine (5 mL) After spin-drying column chromatography, the eluent was (ethyl acetate/petroleum ether = 1/15) to give product 3a as a white solid 24 mg, yield 18percent.

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-3,5-di-tert-butylbenzene, its application will become more common.

Reference:
Patent; UNIV NANKAI; Nankai University; YE MENGCHUN; Ye Mengchun; YANG JINFEI; Yang Jinfei; (18 pag.)CN107840784; (2018); A;,
Bromide – Wikipedia,
bromide – Wiktionary

583-70-0, name is 2,4-Dimethylbromobenzene, 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: C8H9Br

Under a nitrogen atmosphere, cuprous iodide (3.0 mol%, 0.7 mg), sodium iodide (1.0 equiv., 18.7 mg) and magnets were added to a previously baked 10 mL glass pressure tube. Dioxane (0.2 mL), 2,4-dimethylbromobenzene (0.125 mmol, 1.0 equiv., 23.2 mg) and N,N’-dimethylethylenediamine (10.0 mol%, 1.1 mg) were then added. ). After the addition was completed, the glass pressure tube was placed in a metal module that had been preheated to 100 deg C and stirred for 10 hours. After cooling to room temperature, copper powder (20 mol%, 1.6 mg), aluminum chloride (3 mol%, 0.5 mg), N-methylpyrrolidone (0.5 mL) and polymethylhydrogensiloxane (3.0 equiv) were added under a nitrogen atmosphere. ., 83.4mg). The tube was purged of air and charged with carbon dioxide (5.0 equiv., 15 mL) and ammonia gas (5.0 equiv., 15 mL). After the addition was completed, the reactor was placed in a metal module preheated to 160 deg C and stirred for 10 hours. After the reaction was completed, the reaction system was cooled to room temperature and pressure was slowly released. Using dodecane as an internal standard, the yield of the gas chromatogram was determined to be 78%.

The synthetic route of 583-70-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chinese Academy Of Sciences Lanzhou Chemical Physics Institute Suzhou Institute; Li Yuehui; Wang Hua; Dong Yanan; Ke Lisitian·shanduofu; (20 pag.)CN108017557; (2018); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 1422-53-3, 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. 1422-53-3, name is 2-Bromo-4-fluorotoluene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

2-bromo-4-fluorotoluene 25g (132.3mmol, 1.0eq), AIBN 521mg (3.2mmol, 0.024eq),Co(OAc) 2·4H2O 1.6 g (6.5 mmol, 0.049 eq), NaBr 449 mg (4.4 mmol, 0.033 eq), dissolved in HOAc 250 mL (10V)Stir the whole solution, increase the temperature of the outer bath of the reaction coil to 130 C, adjust the coil pressure to 1.2 MPa with oxygen, and start the materialing. The system residence time is 1.5 h and the oxygen is 3 to 5 eq.The system was directly pumped into 375 mL of purified water, and the pH of the system was adjusted to 12-14 with NaOH solids.The aqueous phase was extracted twice with 125 mL MTBE, and the aqueous phase was adjusted to pH 1 with concentrated HCl.A large amount of solid was precipitated, and 11.8 g of the target product was obtained by filtration, yield 41%.

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-Bromo-4-fluorotoluene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Jilinkai Laiying Pharmaceutical And Chemical Co., Ltd.; Hong Hao; Zhang Enxuan; Lu Jiangping; Liu Zhiqing; Li Chao; Tan Yang; (16 pag.)CN110218150; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 583-75-5, 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. 583-75-5, name is 4-Bromo-2-methylaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 70 4-bromo-2-methylaniline (10.5g, 56.3mmol) in 71 acetic acid (300mL) were added 21 NaNO2 (3.89g, 56.3mmol) and 72 water (10mL). After stirring at room temperature for 5h, the reaction mixture was concentrated in vacuo. The residue was diluted with EtOAc and washed with saturated aqueous NaHCO3 solution and brine. The organic layer was dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography (0-50% 73 EtOAc in hexanes) and solidified with hexanes to afford 13 6 as a brown solid (6.81g, 61% yield). 1H NMR (200MHz, CDCl3) delta ppm 7.35-7.43 (m, 1H), 7.45-7.52 (m, 1H), 7.92 (d, J=2.2Hz, 1H), 8.03 (d, J=0.9Hz, 1H); MS ESI/APCI Dual m/z 195 [M-H]-.

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, 4-Bromo-2-methylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Matsuda, Daisuke; Kobashi, Yohei; Mikami, Ayako; Kawamura, Madoka; Shiozawa, Fumiyasu; Kawabe, Kenichi; Hamada, Makoto; Nishimoto, Shinichi; Kimura, Kayo; Miyoshi, Masako; Takayama, Noriko; Kakinuma, Hiroyuki; Ohtake, Norikazu; Bioorganic and Medicinal Chemistry; vol. 25; 16; (2017); p. 4339 – 4354;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 111721-75-6, 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. 111721-75-6, name is 2-Bromo-3-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows.

5-Amino-7-fluoro-1H-quinolin-2-one; To a solution of 2-bromo-3-fluoroaniline (6.5 g, 34.17 mmol) and pyridine (2.7 g, 34.17 mmol) in 20 ml of CH2Cl2, cinnamoyl chloride (5.95 g, 35.88 mol) in 10 ml CH2Cl2 are added dropwise and mixture was refluxed for 30 min. The reaction mixture is diluted with CH2Cl2, the organic layer washed with diluted HCl, saturated Na2CO3 solution, water, and dried (Na2SO4). The solvent is removed in vacuo to give 10.5 g of N-(2-bromo-3-fluorophenyl)-3-phenylacrylamide. To a solution of N-(2-bromo-3-fluorophenyl)-3-phenylacrylamide (10.5 g, 32.8 mmol) in 70 ml of chlor-benzene at 130 C. AlCl3 (21.9 g, 0.164 mol) is added portionwise, the mixture is stirred at this temperature 2 h and poured in ice-water. The precipitate is filtered off and dried. Yield 6.05 g (76%). 6 g (24.8 mmol) of 8-bromo-7-fluoro-1H-quinolin-2-one are refluxed in 30 mL of POCl3 during 2 h, then poured on ice, extracted with benzene, the benzene extract dried (Na2SO4) to yield 6.1 g 8-bromo-2-chloro-7-fluoroquinoline after solvent removal. To a mixture of 10 ml 10%-oleum and 1.4 g (22.2 mmol) of fuming HNO3 8-bromo-2-chloro-7-fluoroquinoline (4.8 g 18.5 mmol) is added portionwise. The mixture is heated at 100 C. for 2 h. Additional HNO3 (0.17 g) is added and stirred for additional 1 h. The reaction mixture is poured in ice-water, extracted with EtOAc, filtered through silica gel, and crystallized from heptane-toluene to yield 2.3 g (50%) 8-bromo-2-chloro-7-fluoro-5-nitroquinoline. 2.3 g (7.54 mmol) of 8-bromo-2-chloro-7-fluoro-5-nitroquinoline are heated at 100 C. for 5 h in a solution containing 16 ml of CH3COOH, 3.2 ml of H2O and 5 ml of conc. HCl. The mixture is poured in water, the formed precipitate is filtered off, stirred in EtOAc and filtered to yield 1.71 g. 8-bromo-7-fluoro-5-nitro-1H-quinolin-2-one. To a suspension 1.7 g (5.92 mmol) of 8-bromo-7-fluoro-5-nitro-1H-quinolin-2-one and 2.3 g (35.5 mmol) of HCOONH4 in 10 ml of ethanol 0.1 g 10% Pd-C are added, and stirred for 2 h at 60 C. A solid disappeared and then formed again. The precipitate is filtered off, dissolved in 3 ml of DMSO and filtered through silica gel. 15 ml of water are added to the eluate, the precipitate is filtered off and dried to yield 0.5 g (47%) 5-Amino-7-fluoro-1H-quinolin-2-one. 1H-NMR (DMSO-d6); delta=6.14 (dd, 1H), 6.20 (dd, 1H), 6.23 (d, 1H), 6.27 (br, 2H), 8.06 (d, 1H), 11.50 (br., 1H).

The chemical industry reduces the impact on the environment during synthesis 2-Bromo-3-fluoroaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Berger, Markus; Rehwinkel, Hartmut; Zollner, Thomas; May, Ekkehard; Hassfeld, Jorna; Schacke, Heike; US2009/137564; (2009); 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. 1295502-53-2, name is 4,7-Dibromo-5,6-difluorobenzo[c][1,2,5]thiadiazole, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 4,7-Dibromo-5,6-difluorobenzo[c][1,2,5]thiadiazole

A mixture of 3,4-difluoro-4,7-dibromobenzothiadiazole (2.9 mmol, 0.92 g) and absolute ethanol (30 mL) were mixed into a 250 mL one-necked flask and NaBH4 (2.9 mmol, 1.13 g) was added at room temperature for 6 h, and the reaction was quenched with 100 mL of distilled water after the reaction. Extracted with methylene chloride, the organic phase washed three times to remove water-soluble impurities and unreacted raw materials, rotary evaporator rotary dry solvent, vacuum drying in white crystalline solid 5. Do not use the purification directly to the next step. (0.75 g, yield: 86%).

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 1295502-53-2.

Reference:
Patent; Central South University; Zou Yingping; Xu Shutao; Chen Guohui; Peng Hongjian; Yuan Jun; Feng Liuliu; (15 pag.)CN106905306; (2017); A;,
Bromide – Wikipedia,
bromide – Wiktionary