Month: March 2021

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. 24358-62-1, name is 1-(4-Bromophenyl)ethylamine, A new synthetic method of this compound is introduced below., Quality Control of 1-(4-Bromophenyl)ethylamine

General procedure: Into a screw cap reaction vial were added a mixture of dry toluene (1.0 mL), immobilized CaLB enzyme (15.0 mg, CaLB-CV-T2-150), the corresponding racemic amine rac-1a-d (0.778 mmol) and the corresponding isopropyl 2-alkoxyacetate 2A-D (1.0 equiv., 0.778 mmol). The reaction mixture was shaken (750 rpm) at 30 C and monitored by taking samples (20 mL) after different reaction times (0.25, 0.5, 1, 2, 3, 4, 6, 8 h). After 8 h, the reactions were worked up.

The synthetic route of 24358-62-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Olah, Mark; Kovacs, Daniel; Katona, Gabriel; Hornyanszky, Gabor; Poppe, Laszlo; Tetrahedron; vol. 74; 27; (2018); p. 3663 – 3670;,
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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. 103-64-0, name is (2-Bromovinyl)benzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of (2-Bromovinyl)benzene

To a solution of N, N-dimethylformamide (DMF) in a volume ratio of 4: 1 with polyethylene glycol 200(PEG-200)) was added 100 mmol of the compound of the above formula (I), 40 mmol of the compound of the above formula (II), 11 mmol of catalyst bis (triphenylphosphine) cyclopentadienyl ruthenium chloride,100 mmol of oxidant bis (trifluoroacetic acid) iodobenzene (PhI (TFA) 2), 20 mmol of organic ligand L1 and 60 mmol of base, 5,7-triazabicyclo [4.4.0] dec-5-ene (TBD) Then the mixture was warmed to 70 C with stirring, and the reaction was stirred at that temperature for 12 hours;After completion of the reaction, the reaction system is naturally cooled to room temperature and the pH is adjusted to neutral, filtered and the filtrate is saturatedSalt water washing, and then extracted with ethyl acetate 2-3 times,The combined organic phases were dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography,Was eluted with a mixture of chloroform and petroleum ether in a volume ratio of 1: 2 to give the compound of the above formula (III) in a yield of 77.3%.

The synthetic route of 103-64-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Huang, Cheng; No proclaimed inventor; (12 pag.)CN106278839; (2017); A;,
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3344-70-5, name is 1,12-Dibromododecane, 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. COA of Formula: C12H24Br2

General procedure: 5,5-dimethylhydantion (3.03 g, 23.6 mmol) and K2CO3 (12.05 g, 87.2 mmol) were dissolved in acetone. Then the mixture were stirred at ambient temperature for 30 min before addition of 3 equivalent 1,6-dibromohexane. After 3 h the acetone solvent was removed by evaporation. 100 mL ethyl acetate was added to extract the product, which were further purified by column chromatography eluting with EtOAc/hexane (3:10, v/v). Compound 8 was obtained as a white powder (6.01 g, 87.7percent). 1H NMR (500 MHz, CDCl3) delta 6.03 (s, H), 3.49 (t, J = 7.0 Hz, 2H), 3.40 (t, J = 6.0 Hz, 2H), 1.89-1.82 (m, 2H), 1.67-1.60 (m, 2H), 1.52-1.41 (m, 8H), 1.37- 1.30 (m, 2H); 13C NMR (126 MHz, CDCl3) delta 177.4, 156.6, 58.7, 38.4, 33.8, 32.6, 27.9, 27.7, 25.8, 25.1. HRMS m/z: [M+H]+ calcd. for C11H20BrN2O2+, 291.0703; found: 291.0700.

The synthetic route of 3344-70-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Li, Lingdong; Zhao, Yuebiao; Zhou, Hao; Ning, Anhong; Zhang, Fengxiang; Zhao (Kent), Zongbao; Tetrahedron Letters; vol. 58; 4; (2017); p. 321 – 325;,
Bromide – Wikipedia,
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Synthetic Route of 937046-98-5, A common heterocyclic compound, 937046-98-5, name is 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine, molecular formula is C6H5BrN4, 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.

Step 1: 7-Methylpyrrolo[2,1-f][1,2,4]triazin-4-amine To a solution of 7-bromopyrrolo[2,1-f][1,2,4]triazin-4-amine (from J & W Pharm Lab, 150 mg, 0.70 mmol) in tetrahydrofuran (2.86 mL) under N2 at rt was added tetrakis(triphenylphosphine)palladium(0) (163 mg, 0.14 mmol). The mixture in a sealed flask was evacuated and refilled with N2 several times, followed by the addition of 2.0 M dimethylzinc in toluene (5.3 mL, 10 mmol) at rt. The reaction mixture was heated at 90 C. for 4 h. The reaction mixture was quenched with ice-water, extracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered, concentrated under vacuum to give the crude, which was purified by prep LC-MS (pH=10 method; XBridge PrepC18 5 mum OBD column, 30*100 mm, 60 mL/min, eluting with a gradient of MeCN and water with 0.15% NH4OH) to afford the desired product as white powders (29.2 mg, 28%). LCMS calcd for C7H9N4 (M+H)+: m/z=149.1. Found: 149.1.

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; Incyte Corporation; Li, Yun-Long; Wang, Xiaozhao; Barbosa, Joseph; Burns, David M.; Feng, Hao; Glenn, Joseph; He, Chunhong; Huang, Taisheng; Mei, Song; Zhuo, Jincong; (169 pag.)US2017/275290; (2017); A1;,
Bromide – Wikipedia,
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Some common heterocyclic compound, 1647-26-3, name is 1-Bromo-2-cyclohexylethane, molecular formula is C8H15Br, 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. Application In Synthesis of 1-Bromo-2-cyclohexylethane

REFERENCE EXAMPLE 13 2-Cyclohexyl-N-(2-hydroxyethyl)ethylamine Hydrochloride (Reference Compound No. 13-1) Anhydrous potassium carbonate (3.5 g) and sodium iodide (9.4 g) are added to a solution of 2-aminoethanol (1.9 ml) and 2-cyclohexylethyl bromide (4.0 g) in ethanol (42 ml), and the mixture is refluxed for 17 hours with stirring. A saturated aqueous ammonium chloride solution is added to the reaction mixture, and the mixture is washed with ether. A 4 N aqueous sodium hydroxide solution is added to the aqueous layer, and the whole is extracted with chloroform. The organic layer is washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue is dissolved in ethyl acetate. To the solution are added a 4 N solution of hydrogen chloride in ethyl acetate (4 ml) and then ether (10 ml) under ice cooling, and the resulting precipitate is filtered off to give 2.2 g (51%) of the titled compound (Reference compound No. 13-1) as crystals. (Reference Compound No. 13-1) mp 158.5~160.2 C.; IR (KBr, cm-1) 3316, 2922, 2856, 1560, 1467, 1454, 1407, 1351, 1084, 1058, 1049, 1001, 932.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1647-26-3, its application will become more common.

Reference:
Patent; Santen Pharmaceutical Co., Ltd.; US6492370; (2002); B1;,
Bromide – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 16518-62-0, name is 3-Bromo-N,N-dimethylaniline, 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 16518-62-0, SDS of cas: 16518-62-0

In a two-necked 200 mL round-bottom flask, Mg turnings (5.30 g, 216 mmol, 10.0 equiv) were flame-dried under vacuum. Upon cooling to room temperature, THF (55 mL), 3-bromo-N,N-dimethylaniline (6.50 g, 32.4 mmol, 1.50 equiv) as a solution in THF (55 mL) and a crystal of I2 were added. The flask was fitted with a reflux condenser and the solution vigorously stirred. Once the resulting exotherm had subsided, the reaction mixture was heated to reflux (70 ¡ãC) for 1h. This Grignard reagent was then allowed to cool to room temperature and added to a cooled solution of 2-bromobenzaldehyde (4.00 g, 21.6 mmol, 1.00 equiv) in THF (32 mL) at 0 ¡ãC via cannula over 10 mm. The reaction mixture was then allowed to reach room temperature and stirred for 12 h and quenched with sat. aq. NH4Cl (75 mL). The aqueous phase was then extracted with EtOAc (3 x 50 mL). The combined organic layers were washed with brine, dried (Na2SO4) and concentrated under reduced pressure. Flash chromatography on silica (1percent to 5percent EtOAc in hexanes) provided the desired (2-bromophenyl)(3-(dimethylamino)phenyl)methanol (S8) (6.36 g, 20.8 mmol, 96percent yield) a yellow viscous oil: Rf 0.4 (20percent EtOAc in hexanes); 1H NMR (500 MHz, CDC13) oe 7.59 (dd, J= 7.7, 1.6 Hz, 1 H), 7.53 (dd, J= 7.9, 1.1 Hz, 1 H), 7.33 (td, J= 7.5, 1.0 Hz, 1 H), 7.20 (t, J= 7.9, 1 H), 7.13 (td, J= 7.7, 1.6 Hz, 1 H), 6.84 (bs, 1 H),6.72 (d, J= 7.5, 1 H), 6.66 (dd, J= 8.2, 2.2 Hz, 1 H), 6.16 (s, 1 H), 2.93 (s, 6 H), 2.38 (bs, 1 H); 13C NMR (125 MHz, CDCl3) oe 150.8, 143.3, 142.9, 132.9, 129.3, 129.1, 128.7, 127.8, 123.1,115.3, 112.2, 111.4, 75.3, 40.8; IR (neat) 3392 (bs), 2917 (s), 2848 (s), 1604 (s), 1498 (s), 1437 (s), 1353 (s), 1018 (m), 996 (s), 744 (s) cm?; HRMS (ES) m/z calculated for C15H17NOBr [M+H] 306.0494, found 306.0492.

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; THE TRUSTEES OF THE UNIVERSITY OF PENNSYLVANIA; HOYE, Adam, T.; KIM, Won-suk; MARTINEZ-SOLORIO, Dionicio; SMITH, Amos, B.; SANCHEZ, Luis; TONG, Rongbiao; NGUYEN, Minh, Huu; WO2013/185021; (2013); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 201138-91-2, 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 201138-91-2 as follows.

In a nitrogen environment 9H-carbazole(100 g, 598 mmol) was dissolved in 2,000 mL of toluene, where the 4,6-dibromodibenzofuran(292 g, 897 mmol), tris(diphenoquinone alkylpiperidinyl) dipalladium (o) (5.48 g, 5.98 mmol), tris-tertbutylphosphine(6.05 g, 29.9 mmol) and sodium tertbutoxide(69.0 g, 718 mmol) sequentially into during heating by and it refluxed 100 C at 35 hours . After the reaction was completed, the reaction solution into water and extracted with dichloromethane (DCM) and then water was removed with anhydrous MgSO4, filter and was concentrated under reduced pressure. In this way, the resulting residue was purified by flash column chromatography to obtain the compound I-15(93.7 g,38%).

According to the analysis of related databases, 201138-91-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Cheil Industries Co., Ltd; Lee, Han Ir; Yu, Uhn Sun; Kang, Dong Min; Kang, Uii Soo; Yang, Yong Tak; Oh, Jae Jin; Yu, Dong Gyu; Lee, Sang Sin; Jang, Yuna; Jung, Su Young; Han, Su Jin; Hong, Jin Suk; (59 pag.)KR2015/6758; (2015); A;,
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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. 64695-79-0, name is 2-Bromo-4,5-difluoroaniline, A new synthetic method of this compound is introduced below., Recommanded Product: 2-Bromo-4,5-difluoroaniline

To a mixture of compound 47a (10 g, 48.08 mmol) and compound 47b (20.84 g, 57.69 mmol) in toluene (200 mL) was added Pd (PPh3) 4 (2.78 g, 2.4 mmol) in one portion under N 2. The resulting black mixture was stirred at 100C for 12 h under N 2. The reaction was cooled to 25C and then treated with 6N HCl (10 mL) with stirring at 25C for 1h. It was diluted with water (400 mL) and extracted with EtOAc (120 mL 3). The combined organic layers was washed with 20%KF solution (200 mL) and brine (100 mL) successively, dried over sodium sulfate and concentrated in vacuum to give the crude product, which was purified by column chromatography on silica gel (5%EtOAc in petroleum ether) to give compound 47c (4.2 g, 51% yield) as a yellow solid. LCMS: R t = 0.709 min in 5-95AB_220&254. lcm chromatography (MERCK RP18 2.5-2mm), MS (ESI) m/z=171.9 [M+H] +. 1H NMR: (400MHz, CDCl 3) delta 7.50 (dd, J=8.8 Hz, 11.2 Hz, 1H), 6.41 (dd, J=6.8 Hz, 12.0 Hz, 1H), 6.37-6.17 (m, 2H), 2.52 (s, 3H).

The synthetic route of 64695-79-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DIZAL (JIANGSU) PHARMACEUTICAL CO., LTD; LI, Zhengtao; ZOU, Hao; ZHU, Wei; SHEN, Changmao; WANG, Rumin; LIU, Wengeng; CHEN, Xiang; TSUI, Honchung; YANG, Zhenfan; ZHANG, Xiaolin; (307 pag.)WO2019/149164; (2019); 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. 33884-43-4, name is 2-(2-Bromoethyl)-1,3-dioxane, A new synthetic method of this compound is introduced below., SDS of cas: 33884-43-4

Sodium hydroxide (3.46g, 1.3 eq) was taken up in water (2OmL) and stirred for about 30 minutes. Then 3-tert-butyl phenol (10.0 g, 66.6 mmol) was added and the resulting mixture was stirred at room temperature for 30 minutes. Next, 2-(2-bromoethyl)-[l,3] dioxane (9.9 mL, 1.1 eq) was added ant the resulting mixture was heated at reflux for 40 hours. The reaction mixture was cooled to room temperature and then added ethyl acetate (150 mL) and with stirring acetic acid was added to pH = 4, followed by dilution with water (100 mL) and ethyl acetate (150 mL). After partitioning, the layers were separated and then washed the organic layer with water (3X 10OmL) and the ethyl acetate layers were dried over magnesium sulfate, filtered and concentrated to give the title compound as a colorless oil (16.9Ig).

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; F. HOFFMANN-LA ROCHE AG; DEWDNEY, Nolan James; HAWLEY, Ronald Charles; KONDRU, Rama K.; LAI, Yingjie; LOU, Yan; WO2010/122038; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 327-52-6,Some common heterocyclic compound, 327-52-6, name is 1-Bromo-2,4,5-trifluorobenzene, molecular formula is C6H2BrF3, 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.

Example 4 Preparation of (3S)-methyl 3-(benzyloxycarbonyl amino)-4-hydroxy-4-(2,4,5-trifluorophenyl)butyrate 116.05 g trifluorobromobenzene and 400 ml tetrahydrofuran were added to a clean flask. The resulting mixture was cooled to -10 to -5 C., and then 864 ml (0.7 mol) methyl magnesium bromide was added thereto dropwisely. The mixture was stirred for 1 hour for use. 23.5 g (S)-methyl 3-(benzyloxycarbonylamino)-4-oxo n-butyrate was dissolved in 300 ml THF, and added dropwisely to the mixture mentioned above and kept at this temperature for 3 hours after completion of the addition. 400 ml solution of ammonium chloride was added dropwisely. Layers were separated. The aqueous layer was extracted with tetrahydrofuran (200 ml*2). The organic layer was dried and concentrated to get 31.4 g (3S)-methyl 3-(benzyloxycarbonylamino)-4-hydroxy-4-(2,4,5-trifluorophenyl)butyrate (yield: 78.5%).

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-2,4,5-trifluorobenzene, its application will become more common.

Reference:
Patent; Zhu, Guoliang; Zhang, Jian; Yang, Lljun; Yao, Qingdan; Ying, Jie; US2012/178957; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary