Month: May 2021

Related Products of 1092349-87-5, 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 1092349-87-5 as follows.

To a stirred solution of 2-bromo-4,5-difluoroaniline [H. Ishikawa, T. Uno, H, Miyamoto, H. Hiraki, H. Tamaoka, M. Tominaga and K. Nakagawa, Chem. Pharm. Bull., 1990, 38(9), 2459-2462] (72 g, 34 mmol) in ether (50 mL) at 0 C. was added sodium carbonate (5.4 g, 44 mmol) and trifluoroacetic anhydride (6.2 mL, 44 mmol). The reaction mixture was stirred at room temperature for 1 h. Water (100 mL) was added and the mixture was extracted with dichloromethane (3*100 mL). The organic extracts were combined, dried (magnesium sulfate), filtered and concentrated in vacuo to give the product (9.9 g, 94%) as a white solid. IR numax (Nujol)/cm-1 3270, 1716, 1550, 1489, 1465, 1226, 1181, 919, 876 and 821; NMR deltaH (400 MHz, CDCl3) 7.45-7.5 (1H, dd, J 7.5 Hz), 8.28-8.34 (1H, dd, J 8 Hz) and 8.36 (1H, br s).

According to the analysis of related databases, 1092349-87-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Vernalis Research Limited; US6706750; (2004); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 121086-19-9,Some common heterocyclic compound, 121086-19-9, name is 4-Bromo-N-isopropylaniline, molecular formula is C9H12BrN, 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: Compound 18a-d (2.55mmol), 8a (2.55mmol), toluene (15mL), ethanol (12mL), NaOH (1.56M, 7mL), Pd(OAc)2 (0.05mmol), PPh3 (0.204mmol), was mixed under N2. The mixture was warmed to reflux for 5h. The mixture was diluted with EtOAc (20mL), washed with water and brine, and dried over MgSO4. The solvent was removed and the residue was separated by silica gel column chromatography using CHCl3/MeOH as an eluent to give 19a-d.

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-N-isopropylaniline, its application will become more common.

Reference:
Article; Liu, Jie; Liu, Qin; Yang, Xue; Xu, Shengtao; Zhang, Hengyuan; Bai, Renren; Yao, Hequan; Jiang, Jieyun; Shen, Mingqin; Wu, Xiaoming; Xu, Jinyi; Bioorganic and Medicinal Chemistry; vol. 21; 24; (2013); p. 7742 – 7751;,
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. 51776-71-7, name is 1-Bromo-4-(difluoromethyl)benzene, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H5BrF2

Synthesis of 4-(difluoromethyl)benzaldehyde (2) To a solution of 1-bromo-4-(difluoromethyl)benzene (1, 35.0 g, 169.08 mmol) in dry tetrahydrofuran (300 mL), n-butyllithium in hexane (2.5 M, 67.0 mL, 169.08 mmol) was added drop wise over a period of 30 min at -78 C. The reaction mass was stirred for 1 h at -78 C. and N,N-dimethylformamide (38.48 mL, 507.24 mmol) was added at same temperature and the reaction was further stirred at -78 C. for 1 h. After completion, the reaction mixture was brought to 0 C. and treated with saturated ammonium chloride solution and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to get the crude. The crude was purified by Combi-flash (40 g, RediSep column) using 2% ethyl acetate in hexanes as eluent. The desired fraction were concentrated below 30 C. under reduced pressure to afford 4-(difluoromethyl)benzaldehyde (2) as light yellow liquid (highly unstable). Yield: 17.0 g, 64%; MS (ESI) m/z poor ionization.

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; eFFECTOR Therapeutics, Inc.; ERNST, Justin T.; REICH, Siegfried H.; SPRENGELER, Paul A.; TRAN, Chinh Viet; PACKARD, Garrick Kenneth; XIANG, Alan X.; NILEWSKI, Christian; MICHELS, Theo; (478 pag.)US2017/145026; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 3722-78-9, name is 8-Bromochroman, 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 3722-78-9, Safety of 8-Bromochroman

EXAMPLE 20 4,5-bis-(4-Chloro-phenyl)-2-chroman-8-yl-4,5-dihydro-1H-imidazole To a solution of 8-bromo-chroman (1.434 g, 6.730 mmol, prepared from 2,6-dibromo-phenol using the procedure reported by Thomas, G. H. et al. Tetrahedron Lett. 1998, 39, 2219-22) in dimethylformamide (10 mL) at room temperature was added zinc cyanide (790 mg, 6.730 mmol). The mixture was degassed by passing argon through for 2 h before tetrakis(triphenylphosphine)palladium (778 mg, 0.673 mmol) was added. The reaction mixture was heated at 90 C. for 12 h. Upon cooling to room temperature, it was diluted with diethyl ether (100 mL) and washed with sodium bicarbonate, brine and dried over anhydrous sodium sulfate. The solid was filtered off, and the filtrate was concentrated in vacuo. Purification of the crude residue by flash chromatography (Biotage system, KP-Sil 32-63 mum, 60 A silica gel) eluding with 10-20% ethyl acetate in hexanes yielded chroman-8-carbonitrile (370 mg, 35%). Hydrogen chloride gas was passed through a solution of chroman-8-carbonitrile (370 mg, 1.736 mmol) in anhydrous ethanol (15 mL) at 0 C. After 1 h, hydrogen chloride gas was stopped and the reaction vessel was sealed with a stopper. After stirring at room temperature for 1 d, the reaction vessel was cooled to 0 C. and the stopper was removed. The solvent was evaporated in vacuo to afford chroman-8-carboximidic acid ethyl ester hydrochloride (491 mg, 88%). It was used without further purification. A solution of meso-1,2-bis-(4-chloro-phenyl)-ethane-1,2-diamine (352 mg, 1.25 mmol), chroman-8-carboximidic acid ethyl ester hydrochloride (491 mg, 2.031 mmol) and triethylamine (350 muL, 2.5 mmol) in ethanol (10 mL) was heated at reflux for 12 h. The solvent was removed and the residue was purified by flash chromatography (Biotage system, KP-Sil 32-63 mum, 60 A silica gel) eluding with 0-5% methanol in ethyl acetate to afford 4,5-bis-(4-chloro-phenyl)-2-chroman-8-yl-4,5-dihydro-1H-imidazole as an off-white foam (189 mg, 36%). HR-MS (ES, m/z) calculated for C24H21N2OCl2 [(M+H)+] 423.126, observed 423.1026.

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, 8-Bromochroman, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hoffmann-La Roche Inc.; US6617346; (2003); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 179737-33-8, 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 179737-33-8 as follows.

In an Ar atmosphere, 20.00 g (73.56 mmol) of 2,3-dibromo-1,4-difluorobenzene, 12.30 g (1.1 equiv, 80.9 mmol) of 2-methoxyphenylboronic acid, 80.92 g (3 equiv, 220.7 mmol) of K2CO3, 4.25 g (0.05 equiv, 3.7 mmol) of Pd(PPh3)4, and 515 mL of a mixed solution of toluene/EtOH/H2O (4/2/1) were sequentially added to a 1,000-mL three-neck flask, and heated and stirred at a temperature of 80 C. for 5 hours. After cooling to room temperature, the reaction solution was extracted therefrom by using toluene. A water layer was removed therefrom, and an organic layer was cleaned by using saturated saline and dried by using MgSO4. MgSO4 was filtered and separated and the organic layer was concentrated. A crude product obtained therefrom was purified by silica gel column chromatography (mixed solvent of hexane and toluene was used in a development layer) to obtain Intermediate IM-1 (16.94 g, yield of 77%). (0394) Intermediate IM-1 was identified by observing the mass number m/z=299 as the molecular ion peak through FAB-MS.

According to the analysis of related databases, 179737-33-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Samsung Display Co., Ltd.; Uno, Takuya; (153 pag.)US2019/389877; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 6938-66-5, 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. 6938-66-5, name is 1-Bromodocosane belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

In argon atmosphere, a DMF solution (2.0 ml) of Compound 23 (85 mg, 0.188 mmol) was ice-cooled, and sodium hydride (60% in oil, 27.0 mg, 0.675 mmol) was added thereto, followed by stirring for 10 minutes under ice-cooling. Then, bromodocosane (110 mg, 0.282 mmol) was added thereto, followed by stirring for 2 hours while gradually raising the temperature of the reaction solution to room temperature. The reaction solution was ice-cooled, and methanol (1 ml) was added dropwise thereto, followed by stirring for 30 minutes. The reaction solution was diluted with ethyl acetate, and saturated sodium bicarbonate water was added thereto, followed by stirring. Then, the organic layer was washed with saturated sodium bicarbonate water and saturated brine in this order and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (toluene : ethyl acetate = 3 : 1, 0.2% triethylamine) to obtain Compound 24-7 (70.2 mg, 49.1%). Developing solvent of Compound 24-7 (toluene : ethyl acetate = 2 : 1) Rf 0.38 C42H81NO10 MW: 760.10 1H-NMR (500 MHz, CDCl3) delta= 5.572 (br.d, 1H, H-5a), 4.909, 4.873 (2d, 2H, J = 6.6Hz, 6.8Hz, OCH2), 4.801-4.616 (m, 6H, 3OCH2), 4.190 (br.d, 1H), 4.112-4.035 (m, 3H), 3.736 (br.d, 1H), 3.406, 3.389, 3.365, 3.345 (4s, 12H, 4OCH3), 3.119 (m, 1H, NCH2), 2.887 (m, 1H, NCH2), 1.67-1.25 (m, 40H, 20CH2), 1.254 (s, 9H, CC(CH3)3), 0.880 (t, 3H, J= 7.1Hz, CH3)

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

Reference:
Patent; SEIKAGAKU CORPORATION; EP1632476; (2006); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 1257535-06-0, These common heterocyclic compound, 1257535-06-0, name is 3-Bromo-4-fluorobenzene-1,2-diamine, 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.

To a stirred solution of compound XXIIb (8.0 g, 0.038 mmol) in dry DMF (800 mL) under nitrogen atmosphere at room temperature were added sodium bicarbonate (3.3 g, 0.0397 mmol) and ethyl bromoacetate (4.49 mL, 0.0397 mmol) successively. The resulting mixture was stirred at 90 C for 30 minutes and 120 C for 5 h. After that, the reaction mixture was diluted with water and extracted with ethyl acetate (2 x 400 mL). The combined organic phase was washed with brine, dried over sodium sulphate and concentrated in vacuo. The obtained crude product was purified by column chromatography using silica gel (230-400 mesh, 30% EtOAc in petroleum ether) to get compound XXIIc as a brown solid. Yield: 6.0 g, 63.69%; LC-MS: Calc. for C8H6BrFN20 245.05; Obs.: 243 [M-H]; 1H NMR (400 MHz, DMSO-d6): delta 9.72 (s, 1H), 6.82 (t, J = 8.68 Hz, 1H), 6.69-6.71 (m, 1H), 6.18 (s, 1H), 3.69 (s, 2H).

Statistics shows that 3-Bromo-4-fluorobenzene-1,2-diamine is playing an increasingly important role. we look forward to future research findings about 1257535-06-0.

Reference:
Patent; BUGWORKS RESEARCH INDIA PVT LTD; PEER MOHAMED, Shahul Hameed; BHARATHAM, Nagakumar; KATAGIHALLIMATH, Nainesh; SHARMA, Sreevalli; NANDISHAIAH, Radha; RAMACHANDRAN, Vasanthi; VENKATARAMAN, Balasubramanian; (221 pag.)WO2018/225097; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 1435-54-7, 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. 1435-54-7, name is 1,3-Dibromo-2-fluorobenzene, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 4. SYNTHESIS OF L-B MOIETIES [0503] Scheme 4-1 : In Step 1 the appropriately substituted dibromo species is coupled with an appropriate boronic acid as known in the art to form a mixture of biaryl and triaryl products from which the desired biaryl compound is isolated. In Step 2 the appropriately substituted biaryl species is converted to the Grignard reagent with activated magnesium. In Step 3 the appropriately substituted aldehyde is treated with the previously prepared Grignard reagent to form an alcohol. In Step 4 the appropriately substituted alcohol is converted to a bromide as known in the art with carbon tetrabromide and triphenyl phosphine. In Step 5 the appropriately substituted bromide is converted to the Grignard reagent with activated magnesium.

The chemical industry reduces the impact on the environment during synthesis 1,3-Dibromo-2-fluorobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAL, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; GREENLEE, William; (317 pag.)WO2017/35413; (2017); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 103275-21-4, A common heterocyclic compound, 103275-21-4, name is 3-Bromo-4-(tert-butyl)aniline, molecular formula is C10H14BrN, 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.

To a solution of 3-bromo-4- tert-butyl-phenylamine (5.00 g, 21.92 mmol) in 80 mL of DCM and 25 mL of methanol was added calcium carbonate (4.39 g, 43.83 mmol), followed by iodinating reagent (8. 55 g, 21.92 mmol). The reaction was stirred for 3 h at room temperature, quenched with water 100 mL, and the product extracted into ethyl acetate (100 mL). The organic layer was washed with brine (75 mL), dried over magnesium sulfate and concentrated. Silica gel chromatography eluting with 25% ethyl acetate/hexane gave the product as an oil (4.50 g, 12.7 mmol, 58%) : H NMR (400 MHz, CDCI3) ; 5 7. 61 (s, 1H), 6.99 (t, J = 0.9 Hz, 1H), 3.96 (s, 2H), 1.44 (s, 9H); MS (ESI) 356.3.

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; ELAN PHARMACEUTICALS, INC.; WO2005/87215; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 3959-05-5,Some common heterocyclic compound, 3959-05-5, name is (2-Bromophenyl)methanamine, 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.

Part A. (2-Bromo-benzyl)-methyl-amine A solution of 2-bromobenzylamine (9 g, 36.1 mmol) in MeOH (60 ml) was added dropwise over 30 min. to a solution of methylamine in MeOH (200 mL of a 2.0 M solution, 0.4 mol). The resulting solution was stirred at rt for 2 h and concentrated. The residue obtained was dissolved in DCM (100 mL) and successively washed with saturated aqueous sodium carbonate, dried over sodium sulphate, and concentrated. The resulting oil was distilled to afford the title compound (7 g, 95%) as a colorless oil (b.p. 110 C. at 0.1 mm Hg, LC/MS retention time=1.22 min.; M+=201.92 Column: Phenominex 4.6 mm*50 mm.

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

Reference:
Patent; Liu, Chunjian; Dhar, T.G. Murali; Gu, Henry H.; Iwanowicz, Edwin J.; Leftheris, Katerina; Pitts, William J.; Herpin, Timothy F.; Pi, Zulan; Bisacchi, Gregory S.; US2002/143176; (2002); A1;,
Bromide – Wikipedia,
bromide – Wiktionary