Tag: M.W=200-300

Electric Literature of 17715-69-4, 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. 17715-69-4, name is 1-Bromo-2,4-dimethoxybenzene, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A suspension of Pd2(dba)3 (6.9 mg, 0.0075 mmol), tBu3PHBF4 (8.7 mg,0.03 mmol), KOH (42 mg, 0.75 mmol), aryl bromide 9 (0.36 mmol) and tetralone 10(0.3 mmol) in a mixture of dioxane/water (4:1, v/v, 3 mL) was degassed and heated under Ar and microwave irradiation (80W of initial power, 100 °C, 40min, infrared probe). Then, the mixture was allowed to cool to rt, diluted in AcOEt, washed with saturated NH4Cl solution, dried over anhydrous Na2SO4,filtered and concentrated under reduced pressure. The crude material was purified by silica gel chromatography.

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

Reference:
Article; Manvar, Dinesh; Fernandes, Talita De A.; Domingos, Jorge L.O.; Baljinnyam, Erdenechimeg; Basu, Amartya; Junior, Eurides F.T.; Costa, Paulo R.R.; Kaushik-Basu, Neerja; European Journal of Medicinal Chemistry; vol. 93; (2015); p. 51 – 54;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 156573-09-0, name is 1-Bromo-4-ethoxy-2,3-difluorobenzene, belongs to ethers-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 156573-09-0, category: ethers-buliding-blocks

Under a nitrogen atmosphere,60 g of trimethylsilylacetylene,120 g of 4-ethoxy-2,3-difluorobromobenzene, 1.9 g of copper iodide,11.7 g of tetrakistriphenylphosphine palladium were dissolved in 500 mL of DMF,And the mixture was stirred at 70 C. for 2 hours.To the reaction mixture were added toluene,Add water,After stirring, the organic layer was separated.The organic layer was washed with waterwater,Ammonia water,Followed by washing with saturated saline in this order,After drying with anhydrous sodium sulfate,The solvent was distilled off under reduced pressure.The obtained crystalRecrystallization and purification by column chromatography (silica gel)120 g of trimethyl- (4-ethoxy-2,3-difluorophenylethynyl) silane was obtained.

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; DIC CORPORATION; NOSE, SAYAKA; SAITOU, YOSHITAKA; KADOMOTO, YUTAKA; (18 pag.)JP5696874; (2015); B2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 62415-74-1, name is 1,2-Dibromo-4-methoxybenzene, belongs to ethers-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 62415-74-1, Product Details of 62415-74-1

General procedure: Into a dried two-necked flask (50 mL) equipped with a condenser were placed a stirrer bar, Mg powder (99.9%, 8 mmol), LiCl (8 mmol),DMI (10 mL), and chlorotrimethylsilane (16 mmol). After stirring the mixture at rt for 15 min, 1,2-dibromoarene (1 mmol) was added and the mixture was stirred for 4 h. The mixture was quenched with sat.NaHCO3 and the resulting precipitates were filtered off. The filtrate was extracted with hexane (3 ×) and the combined organic extracts were washed with brine, dried (anhyd Na2SO4), and concentrated by a rotary evaporator. The crude product was purified by column chromatography (silica gel, hexane or hexane/CH2Cl2).

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, 1,2-Dibromo-4-methoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kitamura, Tsugio; Yamada, Rin; Gondo, Keisuke; Eguchi, Nobuo; Oyamada, Juzo; Synthesis; vol. 49; 11; (2017); p. 2495 – 2500;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 64115-88-4, 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. 64115-88-4 name is 1-Bromo-2-(trifluoromethoxy)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.

Synthesis of (2-amino-5-bromo-pyridin-3-yl)-(2-trifluoromethoxy-phenyl)-methanone To a flame-dried 100 ml round bottomed flask was added 1-bromo-2-(trifluoromethoxy)benzene (2.39 g, 9.9 mmol). The flask was fitted with a rubber septum, purged with nitrogen then charged with anhydrous THF (20 ml). The solution was cooled to -78 C. for 10 min, then a 2.5 M solution of n-butyl lithium in hexanes (3.9 ml, 9.8 mmol) was added dropwise over 3 minutes. The resulting solution was stirred at -78 C. for 40 minutes under nitrogen, then a solution of 739 mg (2.84 mmol) of 2-amino-5-bromo-N-methoxy-N-methyl-nicotinamide in 5 ml of THF was added dropwise over 3 minutes. The resulting red solution was allowed to warm to room temperature over 5 hours, then the reaction was quenched by addition of 10 ml of a saturated aqueous solution of ammonium chloride. Ethyl acetate (50 ml) was added, and the layers were separated. The aqueous fraction was extracted three times with ethyl acetate, and the combined organic fractions were washed with brine, dried (Na2SO4), filtered and concentrated. Purification by flash chromatography on silica gel using a gradient of ethyl acetate in hexanes gave 530 mg (52%) of (2-amino-5-bromo-pyridin-3-yl)-(2-trifluoromethoxy-phenyl)-methanone as a yellow-orange solid. 1H-NMR (CDCl3) delta=8.29 (d, 1H), 7.60 (m, 2H,), 7.45 (t, 1H), 7.42 (m, 3H), 1.79(br. s, 2H); MS m/z: 361 [MH]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-2-(trifluoromethoxy)benzene, and friends who are interested can also refer to it.

Reference:
Patent; SGX Pharmaceuticals, Inc.; US2006/30583; (2006); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 5414-19-7,Some common heterocyclic compound, 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane, molecular formula is C4H8Br2O, 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 solution of (1,3-dioxoisoindolin-2-yl)potassium (10.0 g, 53.9 mmol) and 1-bromo-2-(2-bromoethoxy)ethane (37.5 g, 161 mmol) in acetone (250 mL) was stirred at 60 C. for 12 h. On completion, the reaction mixture was filtered and concentrated in vacuo to give a residue. The residue was purified by column chromatography to give the title compound (12.0 g, 74% yield) as a white solid. 1H NMR (400 MHz, CDCl3) delta 7.91-7.84 (m, 2H), 7.77-7.72 (m, 2H), 3.96-3.90 (m, 2H), 384-377 (m, 4H), 3.42 (t, J==6.0 Hz, 21-).

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-(2-bromoethoxy)ethane, its application will become more common.

Reference:
Patent; Kymera Therapeutics, Inc.; Mainolfi, Nello; Ji, Nan; Kluge, Arthur F.; Weiss, Matthew M.; Zhang, Yi; (1443 pag.)US2019/192668; (2019); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

These common heterocyclic compound, 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, 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. Safety of 1,1-Di-tert-butoxy-N,N-dimethylmethanamine

A stirred suspension of methyl 4-(3,5-dichloro-4-hydroxybenzamido)benzoate (1) (Synthesis 9) (100 mg, 294 mumol) in toluene (2 mL) was heated at 80 C. until homogenous. The resultant solution was treated with 1,1-di-tert-butoxy-N,N-dimethylmethanamine (141 muL, 588 mumol) and the mixture heated at 80 C. for 3 h, and then at RT for 18 h. Additional 1,1-di-tert-butoxy-N,N-dimethylmethanamine (141 muL, 588 mumol) was added and mixture was heated at 80 C. for 5 h. The reaction mixture was cooled to RT and solvent was removed in vacuo. The residue was diluted with water and extracted with Et2O. The organic layer was dried over MgSO4, filtered and concentrated in vacuo. The residue was partially purified by silica gel chromatography (12 g, 0-50% EtOAc in isohexane) to afford methyl 4-(4-(tert-butoxy)-3,5-dichlorobenzamido)benzoate (2) (82 mg, 71%). The material was used in the next step without further purification.

The synthetic route of 1,1-Di-tert-butoxy-N,N-dimethylmethanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KING’S COLLEGE LONDON; US2012/149737; (2012); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 103291-07-2, name is 4-Bromo-1-fluoro-2-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., Formula: C7H6BrFO

Example 2; 2-(4-Fluoro-3-methoxvphenvlV4,4,5.5-tetramethvl-1.3,2-dioxaborolane; Anhydrous 1,2-dimethoxy ethane (12 mL) was added to 4-bromo-l-fluoro-2- methoxybenzene (1.02 g, 5.0 mmol), tris(dibenzylideneaceton)dipalladium (0) (228 mg, 0.25 mmol), tricyclohexylphosphine (209 mg, 0.75 mmol), potassium acetate (732 mg, 7.5 mmol) and 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi-l,3,2-dioxaborolane (1.14 g, 4.5 mmol) and 5 the resulting mixture was irradiated in a microwave at 150 C for 1 h. When cooled to ambient temperature the mixture was filtered and the solvent was evaporated in vacuo to give the crude product: MS (EI) m/z 252 [M+*].

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 103291-07-2.

Reference:
Patent; ASTRAZENECA AB; ASTEX THERAPEUTICS LTD; WO2007/145569; (2007); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 13321-74-9, name is 4-Bromo-2,5-dimethoxytoluene, belongs to ethers-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 13321-74-9, category: ethers-buliding-blocks

General procedure: NaOt-Bu (0.240 g, 2.5 mmol), Pd(OAc)2 (0.006 g, 0.025 mmol) and [HPt-Bu3][BF4] (0.010 g, 0.035 mmol) were suspended in toluene (3 ml) in a 5 ml microwave vial. The appropriate 2-chloroaniline (0.50 mmol) and aryl bromide (0.50 mmol) were then added and the vial sealed. The reaction was then heated in the microwave reactor at 160 C for 3 h, allowed to cool, and then quenched by addition of aqueous HCl (2 M, 3 ml). The organic phase was extracted with CH2Cl2 (2×20 ml), dried (MgSO4), then filtered and the solvent removed under reduced pressure. The crude product mixture was then subjected to column chromatography (SiO2).

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:
Article; Bedford, Robin B.; Bowen, John G.; Weeks, Amanda L.; Tetrahedron; vol. 69; 22; (2013); p. 4389 – 4394;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 588-63-6, name is (3-Bromopropoxy)benzene, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C9H11BrO

To a flame-dried Schlenk tube containing CpFe(CO)2Cl (6) (10.3 mg, 0.05 mmol),3-bromopropyl phenyl ether (1j) (223 mg, 1.04 mmol), THF (0.25 mL), n-BuMgCl (2a)(2M in THF, 0.75 mL, 1.5 mmol), and 1,3-butadiene (90 mL as gas, 4.0 mmol) wereadded successively at ?78 C followed by stirring at 0 °C for 2 h and rt for 22 h. Thereaction was quenched by the addition of sat NH4Cl aq., extracted with Et2O (10 mL x3), concentrated, and purified by PTLC (eluent: hexane/Et2O = 99/1) to obtain heptylphenyl etherS2 (3ja) as yellow oil (79.5 mg, 40percent).

According to the analysis of related databases, 588-63-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Iwasaki, Takanori; Shimizu, Ryohei; Imanishi, Reiko; Kuniyasu, Hitoshi; Kambe, Nobuaki; Chemistry Letters; vol. 47; 6; (2018); p. 763 – 766;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

These common heterocyclic compound, 75148-49-1, name is 3-Bromobenzaldehyde Diethyl Acetal, 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: ethers-buliding-blocks

In an open ChemGlass vial with pressure -release top, a stirred mixture of 3- bromobenzaldehyde diethylacetal (Aldrich, St. Louis, MO) (65 mg, 0.25 mmol), palladium(II) acetate (5.5 mg, 0.025 mmol), 2-dicyclohexylphosphino-2′,6′- diisopropoxybiphenyl (23 mg, 0.05 mmol), K2C03 (138 mg, 1.0 mmol) and trans-2- (trifluoromethyl)cyclopropylboronic acid MIDA ester (99 mg, 0.38 mmol) in toluene (2.5 mL) and H20 (0.5 mL) was de-gassed with N2 for 15 minutes, then the reaction mixture placed under nitrogen, sealed and heated to 100 C and stirred overnight. After allowing to cool, the reaction mixture was diluted with H20 (15 mL) and EtO Ac (20 mL), filtered through Celite and the filter cake washed with EtO Ac (2 x 20 mL). The filtrate was partitioned and the aqueous layer extracted with EtOAc (2 x 15 mL). The combined organic extracts were dried (Na2S04), filtered and concentrated under vacuum to leave a crude residue. The residue was purified by preparative thin-layer chromatography (3 prep TLC plates used) using EtOAc / hexane (1:4) as eluent to give the product (58.6 mg, 69% – yield adjusted for purity) as an oil [note: desired product contaminated with another compound after prep TLC – approximately 85% pure by 1H NMR and LC/MS].[00221] 1H NMR (CDC13, 300MHz): delta 7.34-7.24 (m, 3H), 7.08 (dt, / = 7.1, 1.7 Hz, 1H), 5.46 (s, 1H), 3.67-3.48 (m, 4H), 2.40-2.34 (m, 1H), 1.88-1.75 (m, 1H), 1.40-1.31 (m, 1H), 1.24 (t, 7 = 7.1 Hz, 6H), 1.20-1.14 (m, 1H). 19F NMR (CDC13, 282 MHz): -66.8 (d, / = 6.8 Hz), m/z = no mass-ion by LC/MS or HRMS.

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

Reference:
Patent; RIGEL PHARMACEUTICALS, INC.; DUNCTON, Matthew; SINGH, Rajinder; WO2012/75316; (2012); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem