Month: August 2021

Related Products of 5469-19-2, 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. 5469-19-2, name is 1-Bromo-2,4,5-trimethylbenzene, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 8 3-diethylamino-6-methyl-7-(2′,4′,5′-trimethylanilino)fluoran STR17 30 g. of 3-methoxy-6-acetylaminotoluene, 40 g. of 2,4,5-trimethylbromobenzene, 15 g. of potassium carbonate, 1 g. of copper powder and 0.1 g. of iodine were reacted for 75 hours at 220 to 230 C. Then 15 g. of potassium hydroxide and 30 ml. of iso-propylalcohol were added and refluxed for 24 hours. The resultant was poured into 200 ml. of water and precipitate was filtered off, distilled in a vacuum to obtain 35.5 g. (83 percent of theoretical yields) of 4-methoxy-2,2′,4′,5′-tetramethyldiphenylamine as a light brown crystal having a melting point of 87 to 88 C., and boiling point of 165 to 168 C./3 mmHg.

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-2,4,5-trimethylbenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Yamamoto Kagaku Gosei Kabushiki Kaisha; US4330473; (1982); 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. 68322-84-9, name is 2-Bromo-1-fluoro-4-(trifluoromethyl)benzene, A new synthetic method of this compound is introduced below., Computed Properties of C7H3BrF4

(1) To a solution of Compound 1 (1 g) and Compound 2 (870 mg) in toluene (2.5 mL) was added a solution of potassium bis(trimethylsilyl)amide in toluene (0.5 mol/L, 8.23 mL) under nitrogen atmosphere at room temperature, and then the mixture was heated under reflux for 15 minutes. To the reaction mixture was poured a saturated aqueous solution of ammonium chloride under ice-cooling, and extracted with ethyl acetate. The organic layer was washed with an aqueous solution of hydrochloric acid (1 mol/L), a saturated aqueous solution of sodium hydrogen carbonate, and saturated saline, dried, and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane:ethyl acetate=90:10-80:20) to give Compound 3 (1.08 g) as a pale yellow viscous material. MS (APCI): m/z 333/335 [M-Boc+H]+

The synthetic route of 68322-84-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; YAMAMOTO, Yasuo; SATO, Atsushi; MOROKUMA, Kenji; SHITAMA, Hiroaki; ADACHI, Takashi; MIYASHIRO, Masahiko; (260 pag.)EP3150578; (2017); A1;,
Bromide – Wikipedia,
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These common heterocyclic compound, 40161-54-4, name is 1-Bromo-2-fluoro-4-(trifluoromethyl)benzene, 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. category: bromides-buliding-blocks

3.6-Dihydro-2H-pyran-4-boronic acid pinacol ester (5.62 g, 26.75 mmol), 4-bromo-3-fluorobenzotrifluoride (5.00 g, 20.58 mmol), potassium carbonate (8.53 g, 61.73 mmol) and 1,1?-bis(diphenylphosphino)ferrocenedichloro palladium(II) (753 mg, 1.03 mmol) were suspended in 50 mL of 1,4-dioxane and 10 mL of water. The reaction mixture was refluxed for 3 hrs, solvents were evaporated and the crude was extracted with ethyl acetate (50 mL) and water (50 mL). Organic layer was separated, dried over sodium sulfate and evaporated. The crude obtained was purified by flash chromatography (eluent: cyclohexane/AcOEt; gradient from 40% to 100% of AcOEt) to obtain 4.0 g of the title compound as clear oil.GC-MS (Method 9): Rt=7.76 minMS: m/z=246 (M)+

The synthetic route of 1-Bromo-2-fluoro-4-(trifluoromethyl)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boehringer Ingelheim International GmbH; HOENKE, Christoph; BERTANI, Barbara; FERRARA, Marco; FOSSATI, Giacomo; FRATTINI, Sara; GIOVANNINI, Riccardo; HOBSON, Scott; (88 pag.)US2017/101411; (2017); 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. 626-40-4, name is 3,5-Dibromoaniline, A new synthetic method of this compound is introduced below., Application In Synthesis of 3,5-Dibromoaniline

General procedure: In a nitrogen filled glove box, a 10 mL pressure tube, equippedwith a magnetic stir bar was loaded with the titanium catalyst(0.10 mmol) and dissolved in dry toluene (2 mL). The solutionwas loaded with the aniline derivative (1.0 mmol), alkyne derivative(1.0 mmol) and tert-butylisonitrile (1.5 mmol). The pressuretube was sealed with a Teflon screw cap, taken out of the dry boxand heated at 100 C for 24-48 h in a silicone oil bath. Volatileswere removed in vacuo, and glacial acetic acid (2 mL) was added.The mixture was then heated at 150 C for 24 h. The pressure tubewas then allowed to cool to room temperature, diluted in dichloromethaneand neutralized with saturated NaHCO3 solution. Theorganic layer was further extracted with additional dichloromethane,washed with brine, dried over NaSO4, filtered and concentratedin vacuo. The crude product was dry loaded onto aluminaand purification was accomplished by column chromatography on neutral alumina using hexanes/ethyl acetate (9:1, v/v) as the eluentto provide the desired quinoline.4.1.1. 5,7-Dimethyl-3-phenylquinoline (4)Pale yellow solid 128 mg (55%).

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; McDaniel, Tanner J.; Lansdell, Theresa A.; Dissanayake, Amila A.; Azevedo, Lauren M.; Claes, Jacob; Odom, Aaron L.; Tepe, Jetze J.; Bioorganic and Medicinal Chemistry; vol. 24; 11; (2016); p. 2441 – 2450;,
Bromide – Wikipedia,
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142808-15-9, name is 4-Bromo-2-fluorobenzotrifluoride, 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. Application In Synthesis of 4-Bromo-2-fluorobenzotrifluoride

Step 1: N- (3- (3-fluoro-4- (trifluoromethyl) phenyl) oxetan-3-yl) -2-methylpropane-2-sulfinamide and N- (3- (2-fluoro-3- (trifluoromethyl) phenyl) oxetan-3-yl) -2-methylpropane-2-sulfinamide[0359][0360]Toa solution of 4-bromo-2-fluoro-1- (trifluoromethyl) benzene (0.416 g, 1.7 mmol) in THF (3 mL) was added dropwise n-BuLi (2.5 M in hexane, 0.64 mL, 1.6 mmol) at -78 . The reaction solution was stirred for 1 hat -78 . To the reaction solution was added dropwise a solution of 2-methyl-N- (oxetan-3-ylidene) propane-2-sulfinamide (0.200 g, 1.1 mmol) in THF (7 mL) at -78 . The reaction solution was warmed slowly to room temperature and stirred for 16 h. The reaction solution was quenched with sat? d. aqueous NH4Cl (10 mL) . The mixture was extracted with EtOAc (3 x 30 mL) . The combined organic fractions was washed with brine (2 x 10 mL) , dried with anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by column chromatography over silica gel, usinggradient 0-70of ethyl acetatein petroleum ether as eluent. One isomer of the title compound N- (3- (3-fluoro-4- (trifluoromethyl) phenyl) oxetan-3-yl) -2-methylpropane-2-sulfinamide was obtained as a liquid.1HNMR (400 MHz, CDCl3) delta: 7.70-7.66 (m, 1H) , 7.37 (d, J 8.4 Hz, 1H) , 7.31 (d, J 11.2 Hz, 1H) , 5.10 (s, 2H) , 5.03 (d, J 7.2 Hz, 1H) , 4.87 (d, J 6.8 Hz, 1H) , 1.25 (s, 9H) . Another isomer of the title compound N- (3- (2-fluoro-3- (trifluoromethyl) phenyl) oxetan-3-yl) -2-methylpropane-2-sulfinamide was obtained as a liquid.1HNMR (400 MHz, CDCl3) delta: 7.54-7.49 (m, 3H) , 5.25-5.22 (m, 2H) , 4.88 (d, J 7.2 Hz, 1H) , 4.30 (d, J 6.8 Hz, 1H) , 1.25 (s, 9H) .

The synthetic route of 142808-15-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MORRIELLO, Gregori J.; CHANG, Lehua; FOSTER, Ashley; CHEN, Yili; DWYER, Michael; GUO, Zack Zhiqiang; WANG, Ming; XU, Shimin; BO, Yingjian; FU, Jianmin; (250 pag.)WO2017/277; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 418762-26-2,Some common heterocyclic compound, 418762-26-2, name is 4-Bromo-2-fluoro-5-methylaniline, molecular formula is C7H7BrFN, 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 suspension of 4-bromo-2-fluoro-5- methylaniline (15 g, 73.5 mmol) in 30 mL of concentrated HCl was added 30 mL of water and a solution of NaN02 (5.33 g, 77.2 mmol) in water (20 mL) was added over a 20 minute period at 0C. This diazonium solution was then brought to pH 6 with NaHC03. In a separate vial, a solution of CuS04 (22.9 g, 91.9 mmol) in water (100 mL) was added dropwise to a solution of KCN (23.9 mg, 368 mmol) in water (100 mL) at 0C, then toluene (100 mL) was added and the mixture was stirred and heated to 60C. The previously prepared diazonium solution was added dropwise to the brown CuCN solution at rt for 1 hour and EtOAc (100 ml) was added. The organic phase was washed with brine (200 mL) and concentrated. The crude product was purified via Prep-TLC to afford the 4-bromo-2-fluoro-5-methylbenzonitrile.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-2-fluoro-5-methylaniline, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; PASTERNAK, Alexander; PIO, Barbara; CHOBANIAN, Harry, R.; SHI, Zhi-Cai; DONG, Shuzhi; GUO, Yan; WALSH, Shawn, P.; GUO, Zhiqiang; FERGUSON, Ronald, D.; CATO, Brian; (114 pag.)WO2016/60941; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 7745-91-7, 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. 7745-91-7, name is 3-Bromo-4-methylaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(d) 3-Bromo-4-methylphenol 25 g (134 mmol) of 2-bromo-4-aminotoluene are placed in 400 ml of 1M sulfuric acid in a round-bottomed flask, and the mixture is then cooled to 0 C. 13 g (190 mmol) of sodium nitrite dissolved in 30 ml of water are added, followed by addition of 21 ml of concentrated sulfuric acid. The mixture is refluxed for 4 hours. It is then extracted with ethyl ether. The organic phase is dried over magnesium sulfate, filtered and then evaporated. The residue obtained is purified by chromatography on a column of silica eluted with a mixture of heptane and ethyl acetate (90/10) to give 12.1 g (48%) of the expected product in the form of a brown oil.

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

Reference:
Patent; Bernardon, Jean-Michel; Biadatti, Thibaud; US2003/195259; (2003); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 138526-69-9, 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. 138526-69-9, name is 1-Bromo-3,4,5-trifluorobenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: The amount ratio of the charged material is 3,4,5-trifluorobromobenzene: trimethyl borate = 1:1; Precipitating 28.476 g (0.14 mol) of 3,4,5-trifluorobromobenzene in 70 mL of tetrahydrofuran,Formulation to form a 3,4,5-trifluorobromobenzene solution.In a 1000 mL dry three-necked flask equipped with a thermometer and a constant pressure dropping funnel, 3.8 g of magnesium dust was added.(0.16mol),Tetrahydrofuran (30 mL), 1 mL of 1,2-dibromoethane and 5 mL of the above-prepared 3,4,5-trifluorobromobenzene solution were added dropwise under N2 protection.When the reaction is initiated at 5 to 10 C, a large amount of bubble temperature rises rapidly, and the solution slowly turns grayish black.And controlling the temperature to drop the remaining 3,4,5-trifluorobromobenzene solution (80 mL) of the above configuration at 10 C,The solution slowly turned black-gray, and after the addition was completed, it was kept at 25 C for 2 h.The reaction solution is then cooled to below -30 C (ie, the temperature at which the format reagent reacts with trimethyl borate),Adding a solution of trimethyl borate (dissolving trimethyl borate (14.56 g, 0.14 mol) in 50 mL of tetrahydrofuran to prepare a solution),And keep the temperature stable at -30 ~ -27 C, after the addition of trimethyl borate solution, continue the insulation reaction for 2h.Then, 135 mL of dilute hydrochloric acid having a concentration of 12% was added dropwise to the reaction solution, and the mixture was hydrolyzed at room temperature for 4 hours.After the completion of the hydrolysis reaction, ethyl acetate was added to the reaction mixture to extract a layer (50 mL × 3), and the extract phase was combined.The extract phase was dried over anhydrous sodium sulfate, and the solvent was evaporated to concentrate.Suction filtration to give a small amount of white solid washed with dichloromethane, and dried to give 10.8 g of white powder,That is, 3,4,5-trifluorobenzeneboronic acid represented by the formula (II) was obtained in a yield of 44%.

The synthetic route of 1-Bromo-3,4,5-trifluorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhejiang University of Technology; Li Zhenhua; Zhang Xuchao; Tan Zhiyong; (11 pag.)CN109761820; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 393-37-3, 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. 393-37-3, name is 5-Bromo-2-fluorobenzotrifluoride belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Preparative Example P71 A/-(4-Bromo-2-(trifluoromethyl)phenyl)-2-methylpropane-2-sulfonamide (P71) To a solution of 2-methylpropane-2-sulfonamide (1.00 g, 7.30 mmol) in DMF (10 ml_) was added NaH (60% w/t in mineral oil, 350 mg, 8.80 mmol) at 0C and the solution was stirred for 30 min. Then a solution of 4-bromo-1-fluoro-2-(trifluoromethyl)benzene (1.80 g, 7.30 mmol) in DMF (10 mL) was added and the solution was stirred at 120C overnight, cooled, diluted with H20 and extracted with EA (3x 20 mL). The combined organic phases were dried over Na2S04, filtered, concentrated and purified by CC (PE/EA = 8/1) to afford compound P71 (800 mg, 31%) as a colorless solid.

The synthetic route of 5-Bromo-2-fluorobenzotrifluoride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHENEX PHARMACEUTICALS AG; STEENECK, Christoph; KINZEL, Olaf; GEGE, Christian; KLEYMANN, Gerald; HOFFMANN, Thomas; WO2013/79223; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 627871-16-3, name is 5-Bromo-4-fluoro-2-methylaniline, molecular formula is C7H7BrFN, 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. Quality Control of 5-Bromo-4-fluoro-2-methylaniline

(1 ‘-bis(diphenylphosphino)ferrocene)-dichioropalladium(il) (234 mg, 0,286 mmol), phenylboronic acid (907 mg, 7.44 mmol) and 5-bromo-4-fluoro-2-methylaniline (1.17 g, 5.72 mmol) were dissolved in DME (10 ml). Sodium carbonate aq 2M (5.7 mL, 1 1 mmol) was added, and the mixture was irradiated with microwaves for 2h at 120C. After removing the DME under reduced pressure, the residue was taken with AcOEt (15 mL) and washed with brine (2 x 10 mL). The organic layer was concentrated under reduced pressure and the residue was purified by semi-preparative HPLC-UV, to afford 6-fluoro-4-methyl-[1 ,1 ‘-biphenyl]-3-amine (812 mg, Y = 70%) as a dark oil. MS (ESI+) m/z: 202.1 [M+H]+. (0152) Starting from 6-fluoro-4-methyl-[1 , 1 ‘-biphenyl]-3-amine (751 mg, 3.73 mmol), 3- bromo-N-(6-fluoro-4-methyl-[1 ,1’-biphenyl]-3-yl)benzenesulfonamide was synhesized as described in Procedure B, affording a mixture of mono- and di-sulfonamide, which by hydrolysis with NaOH aq/Dioxane was completely converted to the mono- sulfonamide (1 .41 g, Y = 89%). MS (ESI+) m/z: 442.0 [M+Na]+. (0153) The sulfonamide (1 .03 g, 2.46 mmol) was then coupled with hept-6-ynoic acid (0.63 mL, 4.92 mmol) as described in Procedure B, to afford 7-(3-(N-(6-fluoro-4-methyl- [1 ,1 ‘-biphenyl3-3-yl)sulfamoyl)phenyl)hept-6-ynoic acid (290 mg, Y = 25%). MS (ES+) m/z: 466.2 [M+H]+. (0154) Compound 9 was then obtained by reduction of the alkyne derivative (290 mg, 0.623 mmol) as described for compound 2, as a white solid (235 mg, Y = 80%). 1H NMR (300 MHz, CHLOROFORM-cf) delta ppm 1.20 – 1.33 (m, 4 H) 1 .47 – 1.59 (m, 4 H) 2.01 (s, 3 H) 2.31 (t, J=7.34 Hz, 2 H) 2.58 (t, J=7.56 Hz, 2 H) 6.88 (d, J=10.96 Hz, 1 H) 7.00 (s, 1 H) 7.27 (d, J=7.45 Hz, 1 H) 7.32 – 7.43 (m, 7 H) 7.51 – 7.60 (m, 2 H). MS (ESI+) m/z: 470.2 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 627871-16-3, its application will become more common.

Reference:
Patent; DOMPE’ FARMACEUTICI S.P.A.; DE PIZZOL, Maria; SIRICO, Anna; ZIPPOLI, Mara; BIANCHINI, Gianluca; BECCARI, Andrea; ARAMINI, Andrea; LIBERATI, Chiara Rossana Maria; (53 pag.)WO2018/29150; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary