Month: August 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. 345965-54-0, name is 1-(4-Bromophenyl)cyclopropanamine, A new synthetic method of this compound is introduced below., SDS of cas: 345965-54-0

General procedure: To a solution of (S)-(-)-1-(4-Bromophenyl)ethylamine(0.078 mL, 0.500 mmol) and N,N-diisopropylethylamine(0.131 mL, 0.750 mmol) in dimethylformamide (1.0 mL), 4-(difluoromethoxy)benzene-1-sulfonyl chloride (121 mg, 0.500 mmol)was added. The reaction mixture was stirred at room temperature for 1 hour. LC-MS analysis showed the reaction was complete: 1.4 min, 404.1, 406.1 (MH) Methyl bromoacetate (0.095 mL,1.000 mmol) and BEMP (274 mg, 1.000 mmol) were added to the reaction containing crude (S)-N-(1-(4-bromophenyl)ethyl)-4-(difluoromethoxy)benzenesulfonamide and the reaction was heated at 70 C overnight. The reaction was diluted with ethylacetate and washed with water and brine. The organic portion was dried over sodium sulfate. The solvent was removed, the residue dissolved in methanol and purified by preparative HPLC usinga CH3CN-H2O-TFA solvent system. Obtained methyl (S)-N-(1-(4-bromophenyl)ethyl)-N-((4-(difluoromethoxy)phenyl) sulfonyl)glycinate as light yellow oil.

The synthetic route of 345965-54-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chupak, Louis S.; Zheng, Xiaofan; Hu, Shuanghua; Huang, Yazhong; Ding, Min; Lewis, Martin A.; Westphal, Ryan S.; Blat, Yuval; McClure, Andrea; Gentles, Robert G.; Bioorganic and Medicinal Chemistry; vol. 24; 7; (2016); p. 1455 – 1468;,
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. 112734-22-2, name is (4-Bromo-2-fluorophenyl)methanamine, A new synthetic method of this compound is introduced below., category: bromides-buliding-blocks

1000ml three-necked bottle, in the case of nitrogen 50.0 g of starting material A (211 mmol), 50.7 g of sodium t-butoxide (527 mmol), 0.97 g of Pd2(dba)3 (1.05 mmol),0.87g of S-phos (2.04mmol) and 150ml of xylene, heated to 130 C ~ 140 C, temperature control 130 C ~ 140 C slowly added 43.0g of raw material B (211mmol) and 400ml of xylene mixed solution, add dropwise, Keep warm for 15h, TLC detects the completion of the reaction; cools to room temperature, Filter and filter the cake with xylene. The column liquid was steamed to a non-fraction, and the crude yellow solid was purified with toluene. Drying to obtain 53.2 g of intermediate A, yield: 70%,

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; Yantai Jiu Mu Chemicals Co., Ltd.; Liu Kai; Song Sisi; Wang Peng; Sang Hongjian; Cai Qinggong; Tang Renmao; (23 pag.)CN109369557; (2019); 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. 811711-33-8, name is 1,2-Dibromo-3-fluorobenzene, A new synthetic method of this compound is introduced below., Formula: C6H3Br2F

In a nitrogen atmosphere, a flask containing 114 7-(diphenylamino)-9,9?-dimethyl-9H-fluoren-3-ol (9.0 g), 153 1,2-bromo-3-fluorobenzene (7.9 g), 77 potassium carbonate (8.2 g), and NMP (45 ml) was heated and stirred at a reflux temperature for two hours. After the reaction was stopped, the reaction liquid was cooled to room temperature, and 30 water was added thereto. A precipitate thus precipitated was collected by suction filtration. The obtained precipitate was washed with water and then with Solmix and then purified by silica gel column chromatography (eluent: heptane/toluene=3/1 (volume ratio)) to obtain 12.4 g of 154 6-(2,3-dibromophenoxy)-9,9-dimethyl-N,N-diphenyl-9H-fluoren-2-amine (yield: 84.8%).

The synthetic route of 811711-33-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JNC CORPORATION; FUJITA, Yukihiro; (228 pag.)US2019/165279; (2019); A1;,
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. 1647-26-3, name is 1-Bromo-2-cyclohexylethane belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C8H15Br

Ethyl 1-(2-cyclohexylethyl)-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylate A mixture of 0.4 g of ethyl 4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylate, 0.245 g of 1-bromo-2-cyclohexylethane, 0.18 g of potassium iodide and 0.737 g of potassium carbonate in 15 cm3 of acetonitrile was stirred for 18 hours at a temperature in the region of 70 C. After cooling to about 20 C., the reaction mixture was concentrated to dryness under reduced pressure (5 kPa) at a temperature in the region of 40 C. The evaporation residue was purified by chromatography under atmospheric pressure, on a cartridge of silica gel (Bond Elut; particle size 70-200 mu; mass 12 g), eluding with a mixture of ethyl acetate/40-60 C. petroleum ether (8/2 by volume). The fractions containing the product were combined and then concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40 C. 0.23 g of ethyl 1-(2-cyclohexylethyl)-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylate was obtained. 1H NMR Spectrum (500 MHz, (CD3)2SO-d6, delta in ppm) 0.84 (mt: 2H); 0.98 (t, J=7 Hz: 3H); from 1.00 to 2.65 (mt: 25H); 3.02 (mt: 2H); 3.93 (s: 3H); 3.95 (q, J=7 Hz: 2H); 7.31 (broad s: 1H); 7.35 (broad d, J=9 Hz: 1H); 7.94 (d, J=9 Hz: 1H); 8.67 (broad s: 1H).

The synthetic route of 1647-26-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Baque, Eric; Carry, Jean-Christophe; El-Ahmad, Youssef; Evers, Michel; Hubert, Philippe; Malleron, Jean-Luc; Mignani, Serge; Pantel, Guy; Tabart, Michel; Viviani, Fabrice; US2002/111492; (2002); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 1422-54-4, These common heterocyclic compound, 1422-54-4, name is 2-Bromo-6-fluorotoluene, 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.

Active magnesium (10 mmol) was added in a RB containing dry THF (10 ml) and added a little iodine and stirred the reaction mixture and to this was added compound 1 (in 2 ml THF) slowly and stirred to generate the Grignard reagent. The reaction mixture was cooled to 0 C. and added compound 2 (in THF) drop wise and stirred the reaction mixture at rt for 2 h. After 2 h the reaction mixture was quenched with saturated NH4Cl solution and extracted with EtOAc. The organic layer washed with water, brine, dried over sodium sulphate and evaporated under reduced pressure to obtain compound 3.

Statistics shows that 2-Bromo-6-fluorotoluene is playing an increasingly important role. we look forward to future research findings about 1422-54-4.

Reference:
Patent; CELLIX BIO PRIVATE LIMITED; Kandula, Mahesh; US9175008; (2015); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 53078-85-6,Some common heterocyclic compound, 53078-85-6, name is 2-Bromo-5-methylaniline, 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.

To a suitable amount of a solvent (a mixture of 1,4-dioxane and polyethylene glycol 200 (PEG-200) in a volume ratio of 1: 2.5) was added 100 mmol of the compound of the above formula (I) (II), 6 mmol of a two-component catalyst (1.2 mmol of 1,5-cyclooctadiene (acetoacetate) iridium and 4.8 mmol of bis (tricyclohexylphosphine) nickel chloride (NiCl2(PCy3)2Proline t-butyl ester hydrochloride and 200 mmol NaHS (in the form of a 35% by mass aqueous solution), and then the temperature was raised to 90 C with stirring, and the mixture was stirred at room temperature for 10 minutes. The reaction was stirred at this temperature for 8 hours;After the completion of the reaction, the reaction solution was cooled to room temperature, filtered, and the pH of the filtrate was adjusted to neutral. The extract was shaken with n-hexane for 2-3 times. The organic phase was combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The mixture was eluted with a 2: 1 by volume mixture of chloroform and acetone. The eluate was collected, and the solvent was distilled off under reduced pressure to give the compound of the formula (III) in a yield of 97.4%.

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

Reference:
Patent; Wang, Jianjun; Li, Guiyan; (9 pag.)CN106083729; (2016); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 112734-22-2, 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 112734-22-2 as follows.

A solution of 5-chloro-2-hydroxy-benzoyl chloride (4.00 g, 23.2 mmol) in dichloromethane (46 mL, 0.5 M) was treated with triethylamine (6.46 mL, 46.4 mmol) and 4-bromo-2-fluorobenzylamine (6.10 g, 30.1 mmol). After stirring at room temperature for 16 h, the solution was washed successively with 2 N HCl and saturated aq NaCl. The organic layer was dried over Na2SO4, filtered and concentrated. Purification by MPLC (10-50% ethyl acetate in heptane, 23 mL/min, 70 min) gave N-(4-bromo-2-fluoro-benzyl)-4-chloro-2-hydroxy-benzamide as a white crystalline solid (4.4 g, 53%): mp 159-161 C.; Rf 0.49 (30% ethyl acetate in heptane); 1H NMR (DMSO-d6, 300 MHz) delta 12.56 (br s, 1H), 9.28 (br t, J=5.4 Hz, 1H), 7.88 (d, J=6.0 Hz, 1H), 7.50 (dd, J1=9.9 Hz, J2=1.8 Hz, 1H), 7.37 (dd, J1=8.4 Hz, J2=1.8 Hz, 1H), 7.33 (dd, J1=15.9 Hz, J2=8.1 Hz, 1H), 6.99-6.93 (m, 2H), 4.50-4.46 (m, 2H). ESI-LC/MS m/z calcd for C14H10BrClFNO2: 358.6; found 360.0 (M+1)+. Anal. calcd for C14H10BrClFNO2: C, 46.89; H, 2.81; N, 3.91; Cl, 19.78. Found C, 46.89; H, 2.81; N, 3.90; Cl, 19.73.

According to the analysis of related databases, 112734-22-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; The Institute for Pharmaceutical Discovery LLC; US6420426; (2002); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 129316-09-2, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 129316-09-2 name is 1,3-Dibromo-5-(tert-butyl)benzene, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: [00826] Synthesised according to general procedures GP1 1 – from i) 1 ,3-dibromo-5-(fe/f- butyl)benzene (2.0 g, 6.85 mmol), ‘BuLi (1 .6 M in pentane; 8.5 ml_, 13.6 mmol), THF (70 mL and 5 ml_), dimethyl disulfide (0.74 mL, 8.22 mmol); -78 C?rt; chromatography (EtOAc/cyclohexane 0?10%), 1 .50 g, 85%. ii) (3-bromo-5-(te/ -butyl)phenyl)(methyl)sulfane (1 .50 g, 5.79 mmol), m-CPBA (77%; 2.50 g, 1 1 .1 mmol), DCM (50 mL); rt, 12 h; chromatography (EtOAc/cyclohexane 0?30%), 1 .40 g, 83%. NMR (500 MHz, CDCI3) delta 7.87 (t, J = 1 .6 Hz, 1 H), 7.85 (t, J = 1 .6 Hz, 1 H), 7.76 (t, J = 1 .7 Hz, 1 H), 3.05 (s, 3H), 1 .32 (s, 9H). General procedures GP11 (1119) [00687] ‘BuLi was added dropwise over 20 min to a solution of 1 ,3-dibromo-5-(fe/?-butyl)benzene in THF at -78 C and stirring was maintained at -78 C for 10 min. A solution of disulfide (RSSR) in THF was added dropwise over 20 min at the same temperature and the reaction was warmed slowly to rt. Sat. NH4CI was added. The aqueous phase was extracted with EtOAc (3 x). The combined organic phase was dried over MgSC , filtered and the solvent was removed under reduced pressured. The crude was purified by chromatography (1120) [00688] m-CPBA was added in small portions to a solution of the intermediate sulfide in DCM. The mixture was stirred at rt for 12 h and diluted with EtOAc. The solution was washed with sat. NaHCC (3 x), dried over MgSC , filtered and the solvent was subsequently removed under reduced pressure. The crude was purified by chromatography

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,3-Dibromo-5-(tert-butyl)benzene, and friends who are interested can also refer to it.

Reference:
Patent; THE INSTITUTE OF CANCER RESEARCH: ROYAL CANCER HOSPITAL; SPRINGER, Caroline; MARAIS, Richard; NICULESCU-DUVAZ, Dan; LEUNG, Leo; SMITHEN, Deborah; CALLENS, Cedric; TANG, Haoran; (403 pag.)WO2017/141049; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 1003-99-2, 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. 1003-99-2, name is 2-Bromo-5-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 2-bromo-5-fluoroaniline (1.0 eq.) in tetrahydrofuran (0.2 M) at O0C under N2 atmosphere was added dropwise IM NaHMDS (2.5 eq.) The reaction was stirred for 15 minutes at 00C, and a solution of di-tert -butyl dicarbonate in tetrahydrofuran was added. The reaction was warmed to room temperature overnight. The solvent was evaporated, and the resulting residue was quenched with 0.1N HCl aqueous solution. The aqueous suspension was extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous MgSO4, and concentrated en vacuo. The crude material was purified by flash chromatography on a COMBIFLASH.(R). system (ISCO) using 0-5percent ethyl acetate in hexane to give the product as light yellow oil.

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

Reference:
Patent; IRM LLC; NOVARTIS AG.; WO2009/111337; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 10546-67-5,Some common heterocyclic compound, 10546-67-5, name is 2,6-Dibromo-4-(tert-butyl)aniline, molecular formula is C10H13Br2N, 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 stirring solution of 2,6-dibromo-4-tert-butylaniline in 115 mL of EtOH was added 11.5 mL of concentrated H2SO4. To the stirring solution at 90 0C was added 8.8 g of NaNO2 in several portions. After 37 h, EtOAc and 120 mL of H2O were added, and the layers separated. The organic layer was washed with 40 mL of brine, dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (hexanes) provided 8.15 g of l,3-dibromo-5-tert-butylbenzene as a yellow-brown oil with some impurity.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,6-Dibromo-4-(tert-butyl)aniline, its application will become more common.

Reference:
Patent; COMENTIS, INC.; PURDUE RESEARCH FOUNDATION; WO2009/42694; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary