Month: February 2021

Application 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.

To a solution of 4-bromo-2-fluoro-5-methylaniline (1.10 g, 5.39 mmol), ethyl 4-(3-methylbutanoyl)benzoate (1.26 g, 5.39 mmol) and Et3N (2.25 ml, 16.2 mmol) in DCM (100 ml) was added TiCl4 (2.7 ml, 2.7 mmol) dropwise and the reaction was monitored by TLC. The mixture was kept stirring at room temperature for 16 h, then 5N NaOH was added to adjust pH = 14, extracted with DCM and the organic layer was washed with brine, dried and concentrated. The resulting residue was used for the next step reaction directly.

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:
Article; Song, Fengbin; Xu, Guozhang; Gaul, Michael D.; Zhao, Baoping; Lu, Tianbao; Zhang, Rui; DesJarlais, Renee L.; DiLoreto, Karen; Huebert, Norman; Shook, Brian; Rentzeperis, Dennis; Santulli, Rosie; Eckardt, Annette; Demarest, Keith; Bioorganic and Medicinal Chemistry Letters; vol. 29; 15; (2019); p. 1974 – 1980;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 460-00-4, 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. 460-00-4, name is 1-Bromo-4-fluorobenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: 7a was prepared by reacting compound 6 (4.00g, 18.1mmol) with 4-bromoanisole (3.38g, 18.1mmol) in the presence of Pd(PPh3)4 and Na2CO3 (6.40g, 60mmol) in THF (80mL containing 10% water). After refluxing for 15h at 368K, the product was extracted with CH2Cl2. The organic layer was dried over MgSO4, filtrated, and evaporated. Column chromatography on SiO2 with petroleum ether as the eluent afforded 3.99g of 7a as a yellowish solid in 78% yield.

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

Reference:
Article; Liu, Hongliang; Pu, Shouzhi; Liu, Gang; Chen, Bing; Dyes and Pigments; vol. 102; (2014); p. 159 – 168;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 583-70-0,Some common heterocyclic compound, 583-70-0, name is 2,4-Dimethylbromobenzene, molecular formula is C8H9Br, 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: To a three-necked, 50mLflask equipped with a magnetic stirring bar, 15mL of THF, 2.5mmol of ester(1 equiv), 0.375mmol of CuO (15%equiv), 7.5 mmol of aryl halides and magnesium chips (3 equiv) or 15mmol ofalkyl bromides and magnesium chips(6 equiv) were added. The reaction mixturewas heated at 65 Cfor 4 h. Theprogress of the reaction was monitored by TLC. Then, the reaction was quenchedby saturated aqueous NH4Cl (5 mL), extracted with AcOEt (10 mL ¡Á 3),dried over sodium sulfate, filtered, and evaporated to give the raw product.Pure product could be obtained by TLC with petroleum /AcOEt = 5/1 as eluent

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

Reference:
Article; Gao, Fei; Deng, Xiang-Jun; Tang, Yu; Tang, Jin-Peng; Yang, Jun; Zhang, Yuan-Ming; Tetrahedron Letters; vol. 55; 4; (2014); p. 880 – 883;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route 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.

EXAMPLE 192 1,2-Dihydro-6-(3-nitrophenyl)-2,2,4,8-tetramethylquinoline (Compound 292, structure 86 of Scheme XXII, where R1 =R3-5 =H, R2 =nitro) 4-Bromo-2-methylaniline (5.58 g, 30 mmol) was treated with iodine (0.2 g, 0.9 mmol) and acetone (150 mL) in a sealed tube at 80 C. for 24 h to provide 6-bromo-1,2-dihydro-8-methylquinoline (Compound 85 of Scheme XXII) in 9 % yield as a yellow oil (0.70g). Most of the aniline (>80%) was recovered.

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:
Patent; Ligand Pharmaceuticals Incorporated; US5696133; (1997); 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. 452-74-4, name is 1-Bromo-2-fluoro-4-methylbenzene, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H6BrF

A: A mixture of 4-bromo-3-fluorotoluene (39.4 g, 0.21 mol), NBS (38.1 g, 0.22 mol) and ADBN (5 g, 0.03 mol) in 250 mL CH2Cl2 was heated at reflux for 6 h. After cooling to room temperature, the reaction mixture was filtered, and the filtrate was washed with water, brine, and concentrated under vacuum to afford l-bromo-4-(bromomethyl)-2-fluorobenzene, which was used without further purification.

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; MERCK & CO., INC.; WO2008/51404; (2008); A2;,
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. 16518-62-0, name is 3-Bromo-N,N-dimethylaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: 3-Bromo-N,N-dimethylaniline

TO A MIXTURE OF] [PALLADIUM (II)] acetate (3 mg, 5 [MOLpercent),] [2-DICYCLOHEXYLPHOSPHINO-2APOS;- (N,] N- dimethylamino) biphenyl (10 mg, 5 molpercent) and lithium bis (trimethylsilyl) amide (0.55 mL, 0.55 mmol, 1.1 equiv, 1.0 M solution in tetrahydrofuran) in toluene (0.5 mL) under nitrogen at-10 [¡ãC,] was added a solution of [3- [5- (3, 4-DICHLORO-] [PHENYL)-1-(2, 4-DICHLORO-PHENYL)-1H-PYRAZOL-3-YL]-PROPIONIC] acid tert-butyl ester (243 mg, 0.50 mmol, 1.0 equiv) in toluene (1.0 mL). This mixture was stirred at [- 10 ¡ãC] for 10 min, then (3-bromo-phenyl)-dimethyl-amine (42 mg, 0.21 mmol, 0.45 equiv) in toluene (0.5 mL) was added. The resulting solution was allowed to warm to room temperature then was heated to 80 [¡ãC] for 3 h. The reaction mixture was cooled to room temperature, and the reaction was quenched with satd aq ammonium chloride (1.0 mL). Water (10.0 mL) was added, and the resulting mixture was extracted with diethyl ether (2 x 10 mL). The combined extracts were washed with brine (10 mL), dried [(NA2SO4),] and concentrated under reduced pressure. The crude material was purified by reversed-phase HPLC to afford the desired aryl acetic acid ester (20 mg, 16percent). MS [(ESI)] : mass [CALCULATED FOR C30H29CI4N302,] 603.10 ; [M/Z] found, 604.1 [M+H] [+.]

The synthetic route of 16518-62-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA, N.V.; WO2004/7463; (2004); 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. 7073-94-1, name is 1-Bromo-2-isopropylbenzene, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 7073-94-1

7 g of 2,4,6-trimethylaniline, 10 g of 2-chlorotoluene, 11 g of sodium t-butoxide, 75 mL of toluene was added to the flask, And the mixture was thoroughly stirred under a nitrogen stream. here, Palladium acetate 24 mg, 85 mg of 1,3-bis (2,6-diisopropylphenyl) imidazolium chloride was added, The reaction solution was raised to 110 C., And the mixture was stirred for 3 hours. The obtained reaction solution was cooled and poured into water, And extracted with ethyl acetate. The obtained organic phase was dried over sodium sulfate, After concentration, purification by silica gel column chromatography (developing solution: ethyl acetate / hexane = 1/20) gave 10 g of intermediate 403A.

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 7073-94-1.

Reference:
Patent; FUJIFILM CORPORATION; YAGI, KAZUNARI; TATEISHI, KEIICHI; (89 pag.)JP2017/66208; (2017); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 1073-06-9, The chemical industry reduces the impact on the environment during synthesis 1073-06-9, name is 1-Bromo-3-fluorobenzene, I believe this compound will play a more active role in future production and life.

1)3 Grignard reagent was prepared from 3-bromofluorobenzene (8.20 mL, 75.0 mmol) and magnesium (1.9095 g, 78.5 mmol) in dry THF (120 mL) in virtually quantitative yield. To a solution of ethyl formate (2.42 mL, 30.0 mmol) in dry THF (60 mL) a solution of Grignard reagent solution was slowly added at 0 C. After 1 h warming to room temperature, the reaction mixture was quenched with sat. NH4Cl aq. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layer was dried over MgSO4, and filtered. The filtrate was concentrated in vacuo. The resulting residue was purified by column chromatography on silica gel (hexane/ ethyl acetate = 30/1) to afford bis(3-fluorophenyl)methanol. Yellow oil (6,6738g, quant.). 1H NMR (500 MHz, CDCl3) delta 7.34-7.27 (m, 2H), 7.17-7.04 (m, 4H), 7.02-6.93 (m, 2H), 5.81 (d, J = 3.5 Hz, 1H), 2.32 (d, J = 3.5 Hz, 1H) 4

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, 1-Bromo-3-fluorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Tanaka, Kenta; Kishimoto, Mami; Hoshino, Yujiro; Honda, Kiyoshi; Tetrahedron Letters; vol. 59; 19; (2018); p. 1841 – 1845;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 18087-73-5,Some common heterocyclic compound, 18087-73-5, name is 3-Bromoimidazo[1,2-b]pyridazine, molecular formula is C6H4BrN3, 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.

Unit Operation 1.1: 1 Sonogashira Reaction AP24595, palladium tetrakis triphenylphosphine (Pd(PPh3)4) , copper (I) iodide (Cul), triethylamine, and tetrahydrofuran (THF) are charged to the reactor. The mixture is stirred and degassed with nitrogen and then pre-degassed AP28141 is charged. The resulting mixture is brought to 45 – 55C and held for not less than 3 hours. The reaction completion is determined by IPC-1 (HPLC). If the IPC-1 criterion is met, the mixture is concentrated to a target volume and cooled. Unit Operation 1.2: Deprotection / 2nd Sonogashira Reaction AP25570, additional palladium tetrakis triphenylphosphine (Pd(PPh3)4), copper (I) iodide (Cul), and tetrahydrofuran (THF) are charged to the reactor. The mixture is concentrated and the water content is determined by IPC-2 (KF). If the IPC-2 criterion is met, the mixture is warmed to 45 – 60C and 25% sodium methoxide solution in methanol is slowly added. The reaction mixture is stirred and held for 30 – 60 minutes at 45 – 55C. The reaction progress is determined by IPC-3 (HPLC). The reaction mixture may be held at a lower temperature during the IPC analysis. If the IPC-3 criterion is met, the process is continued to Unit Operation 1.3. Unit Operation 1.3: Isolation of AP25047 HCI While stirring, the cool reaction mixture is quenched by addition of hydrogen chloride gas. A precipitate forms, and residual hydrogen chloride is removed from the suspension by a nitrogen purge. Tetrahydrofuran (THF) is replaced with toluene by an azeotropic distillation under reduced pressure. The resulting warm slurry is filtered in an agitated filter dryer and the filter cake is triturated and washed with warm toluene. The content of process impurity AP291 16 is determined by IPC-4 (HPLC). If the IPC-4 criterion is met, the wet filter cake is dried with agitation under a flow of nitrogen and reduced pressure at 35 – 45C (jacket temperature). The drying is monitored by IPC-5 (LOD, gravimetric). If the IPC-5 criterion is met, the crude AP25047 HCI is discharged and packaged in FEP bags in a plastic container. The isolated AP25047 HCI can be held for up to 7 days prior to forward processing. Unit Operation 1.4: Work-up The crude AP25047 HCI solid is charged to a reactor with dichloromethane (DCM) and washed with aqueous ammonia. The aqueous phase is back extracted with DCM for yield recovery purposes and the combined organic phase is washed a second time with aqueous ammonia. The organic layer is then washed with aqueous hydrochloric acid until the aqueous phase reaches a pH of 1-2, as indicated by IPC-6 (pH strips). If the IPC-6 criterion is met, the organic phase is treated with aqueous sodium bicarbonate until the aqueous wash reaches a pH of NLT 7, as indicated by IPC-7 (pH strips). The organic phase is briefly concentrated followed by the addition of fresh dichloromethane. The organic solution is passed through a silica gel pad, which is then rinsed with additional fresh dichloromethane for increased product recovery. Unit Operation 1.5: Crystallization of AP25047 The dichloromethane solution is concentrated under reduced pressure, and the dichloromethane is replaced with 2-propanol by azeotropic distillation under reduced pressure to the targeted final volume range. The resulting suspension is then cooled and further aged with agitation. Unit Operation 1.6: Isolation / Drying The precipitated product is isolated in an agitated filter dryer under a flow of nitrogen, and the filter cake is rinsed with 2-propanol. The wet filter cake is dried with agitation under a flow of nitrogen and reduced pressure at 45 – 55C (jacket temperature). The drying is monitored by IPC-8 (LOD, gravimetric). If the IPC-8 criterion is met, the product is sampled and packaged into polyethylene bags and placed within a heat sealed mylar coated aluminum foil bag, within an HDPE shipping container (Expected yield range, 65 – 89%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Bromoimidazo[1,2-b]pyridazine, its application will become more common.

Reference:
Patent; ARIAD PHARMACEUTICALS, INC.; MURRAY, Christopher, K.; ROZAMUS, Leonard, W.; CHABER, John, J.; SHARMA, Pradeep; WO2014/93579; (2014); A2;,
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. 6274-57-3, name is 1-(4-Bromophenyl)-N,N-dimethylmethanamine, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 1-(4-Bromophenyl)-N,N-dimethylmethanamine

2.33.a tert.butyl 4-(4-dimethylaminomethyl-phenyl)-4-hydroxy-piperidine-1-carboxylate 236 mL (0.38 mol, 1.6M in hexane) n-BuLi is added dropwise over 35 min at -65 C. to a solution of 81 g (0.38 mol) of 4-bromodimethylbenzylamine in 450 mL THF. 75 g (0.38 mol) of tert.butyl 4-oxo-piperidine-1-carboxylate in 150 mL THF are added dropwise over 60 min, so that the temperature does not exceed -60 C. The reaction solution is stirred for 2 h at -65 C. and for a further 17 h at ambient temperature. The reaction mixture is combined with 300 mL ether, cooled to 5 C. and the precipitate formed is suction filtered. The precipitate is combined with 200 mL water and 700 mL ether and stirred for 10 min. The organic phase is dried over magnesium sulphate and the solvent eliminated using the rotary evaporator. The product obtained is dried in vacuo. Yield: 45 g (35.7% of theory).

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 6274-57-3.

Reference:
Patent; Boehringer Ingelheim International GmbH; US2004/242572; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary