Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 53078-85-6, name is 2-Bromo-5-methylaniline, 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 53078-85-6, HPLC of Formula: C7H8BrN

Synthesis of Starting CompoundsPreparation of tert-butyl 5-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate (A-1)Step 1: tert-butyl 2-bromo-5-methylphenylcarbamateTo a solution of 2-bromo-5-methylaniline (1.0 eq.) in tetrahydrofuran (0.2 M) at 0 C. under N2 atmosphere was added dropwise 1M NaHMDS (2.5 eq.). The reaction was stirred for 15 minutes at 0 C., 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 system (ISCO) using 0-5% ethyl acetate in hexane to give tert-butyl 2-bromo-5-methylphenylcarbamate as a light yellow oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-5-methylaniline, and friends who are interested can also refer to it.

Reference:
Patent; IRM LLC; Novartis AG; US2011/53893; (2011); 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. 6911-87-1, name is 4-Bromo-N-methylaniline, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H8BrN

General procedure: To a solution of glycosyl 13/methyl glucoside37,38 20/33 (0.175 mmol) in dry DMF was added aniline or N-alkylated aniline (0.262 mmol), respectively, followed by anhyd K2CO3 (0.436 mmol). The mixture was stirred at 60 C under a N2 atmosphere until TLC analysis indicated the disappearance of the carbohydrate starting material (12-36 h). After completion of the reaction, the mixture was allowed to cool down to r.t. The solution was then diluted with water (10 mL) and the aqueous phase was extracted with Et2O (3 ¡Á 10 mL). The combined organic phases were washed with brine, dried (MgSO4), filtered, and evaporated. The residue was purified by column chromatography (silica gel; EtOAc-hexane, 1:9).

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:
Article; Moshapo, Paseka T.; Kinfe, Henok H.; Synthesis; vol. 47; 23; (2015); p. 3673 – 3686;,
Bromide – Wikipedia,
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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. 57807-28-0, name is 1-Bromo-2-cyclopropylbenzene, A new synthetic method of this compound is introduced below., Application In Synthesis of 1-Bromo-2-cyclopropylbenzene

Under nitrogen atmosphere, at RT, the compound of the formula (32-4) 1.76 g was dissolved in tetrahydrofuran 9 ml. The resulting solutions were cooled to ?78¡ã C. and thereto added n-butyllithium 6.6 ml (1.6M hexane solution) and the resulting mixtures were stirred for 30 minutes. Thereafter, to the resulting mixtures was added a suspension of trichlorobismuth 939 mg in tetrahydrofuran 5 ml and the resulting mixtures were stirred for 1 hour with heating to rt. To the resulting reaction solutions was added water 20 ml and the resulting mixtures were extracted with chloroform. The resulting chloroform layers were washed with saturated saline, dried over anhydrous magnesium sulfate and then filtered, and the resulting filtrates were concentrated under reduced pressure to give the compound of the formula (33-4) 2.27 g as crude products.

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; Nakashima, Yosuke; Jin, Yoshinobu; Konobe, Masato; US2014/228219; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 656-64-4,Some common heterocyclic compound, 656-64-4, name is 3-Bromo-4-fluoroaniline, molecular formula is C6H5BrFN, 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.

Compound 3 (80g, 0.4923mo1), compound 4 (280g, 1.474 mol) and ethanol (2.4L) were added into the reactor, then the reactor was heated to reflux for 1 hours, then the mixture was concentrated, and the crude product was washed with n-hexane/ethyl acetate (200mL, V/V=10: 1) , filtered, dried to obtain compound 5(138g, yield 88.7%).MS: 316 [M+lfb. ?H-NMR(400Hz, DMSO-d6): 11.42 (s, 1 H), 8.86 (s, 1 H), 7.17 (dd, 1 H), 7.08 (dd, 1H), 6.77 – 6.71 (m, 1 H), 6.24 (s, 2 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Bromo-4-fluoroaniline, its application will become more common.

Reference:
Patent; XU, Yong; HUANG, Lu; (26 pag.)WO2017/124822; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 1073-06-9,Some common heterocyclic compound, 1073-06-9, name is 1-Bromo-3-fluorobenzene, molecular formula is C6H4BrF, 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: 2-Bromo-6-fluorobenzaldehydeTo a stirred solution of diisopropylamine (1.4 mL, 0.00571 mol) in dry tetrahydrofuran (7.2 mL) was added dropwise n-butyllithium (1.6M in hexane) (3.56 mL, 0.00571 mol) at 0C and stirring was continued for 15 min at 0C. The reaction mixture was cooled to -78C and l-bromo-3-fluorobenzene (1 g, 0.00571 mol) was added over 10 min. After stirring for 1 h at -78C, anhydrous N,N-dimethylformamide (7.2 mL) was added dropwise over 5 min and the resulting mixture was stirred for another 20 min at -78C. The reaction was quenched with addition of acetic acid (0.6 mL) followed by water (15 mL) and the mixture was warmed to room temperature. The mixture was extracted with ethyl acetate (2×20 mL) and the combined organic layers were washed with water (2×10 mL) followed by brine solution and dried over anhydrous sodium sulfate. The solvent was evaporated under vacuum to afford the title compound as a pale yellow solid (850 mg, 73%). H NMR (400 MHz, DMSO-d6) : delta 10.21 (s, 1H), 7.66-7.61 (m, 2H), 7.45-7.42 (m, 1H). ESI-MS: Calculated mass: 201.94; Observed mass: 202.0 [M]+.

The synthetic route of 1073-06-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASANA BIOSCIENCES, LLC; THOMPSON, Scott, K.; SMITH, Roger, A.; REDDY, Sanjeeva; JOHN, Tyler, M.; NYAVANANDI, Vijay, Kumar; SUBRAMANYA, Hosahalli; POTLURI, Vijay; PANIGRAHI, Sunil, Kumar; NADIPALLI, Prabhakara, Rao; SENGUPTA, Saumitra; WO2014/169167; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 1647-23-0,Some common heterocyclic compound, 1647-23-0, name is 1-Bromo-3,3-dimethylbutane, molecular formula is C6H13Br, 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.

Ste S; The grignard reagent was made as follows: Magnesium turnings (2.4 g, 100 mmol) were suspended in dry Et2O (150 ml) under N2. A few iodine crystals were added to the mixture. The 1 -bromo-3,3-diemthyl butane (16.5 g, 100 mmol) in Et20 (50 ml) was added in portions over ~ 45 minutes to maintain gentle reflux. After the addition of all of the 1-bromo-3,3-diemthyl butane, the reaction was refluxed for 2 nr. The gringnard solution was used as is in the next step.The grignard reagent (100 mmol in 200 ml of Et20) was added to a solution of the imine (9.9 g, 33.5 mmol) at -78C. The solution was siowly warmed to RT. After stirring at RT for 2 h, the reaction was quenched with sat. NH4CI(aq.) at 0 C. Ethyl acetate was added, and the mixture was stirred at RT for 1 h. The layers were separated, and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine and dried (MgS04). The mixture was filtered and concentrated. The residue was purified via gradient flash chromatography (0-40% EtOAc in hexanes, SiO2). The major fraction was recrystallized from heptane/IPA which yielded 2.8 g of the desired product. The mother liquor was recrystallized once again to provide an additional 1.3 g (32 % total).

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-3,3-dimethylbutane, its application will become more common.

Reference:
Patent; SCHERING CORPORATION; WONG, Michael, K.; LAVEY, Brian, J.; YU, Wensheng; KOZLOWSKI, Josheph, A.; DEMONG, Duane, E.; DAI, Xing; STAMFORD, Andrew, W.; MILLER, Michael, W.; ZHOU, Guowei; YANG, De-Yi; GREENLEE, William, J.; WO2011/119559; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 54879-20-8, 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. 54879-20-8, name is 2-Bromo-3-methylaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 2-bromo-3-methylaniline (1.0 eq.) in tetrahydrofuran (0.2 M) at 0¡ã C. under N2 atmosphere was added dropwise 1M NaHMDS (2.5 eq.). The reaction was stirred for 15 minutes at 0¡ã C., 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? system (ISCO) using 0-5percent ethyl acetate in hexane to give product as light yellow oil.

The synthetic route of 2-Bromo-3-methylaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GlaxoSmithKline Biologicals SA; Skibinski, David; Jain, Siddhartha; Singh, Manmohan; O’Hagan, Derek; (124 pag.)US9408907; (2016); B2;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 2695-48-9,Some common heterocyclic compound, 2695-48-9, name is 8-Bromo-1-octene, 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.

General procedure: (9RS,12S)-Isomer A Grignard reagent was prepared from 1-bromo-7-octene (6.80 g, 36 mmol) and Mg (1.08 g, 45 mmol) in dry THF (30 mL) in the presence of a small amount (20 mg) of I2 under argon. A solution of (S)-7 (5.77 g, 26 mmol) in dry THF (10 mL) was added dropwise to the ice-cooled and stirred Grignard reagent at 0-10 C. Stirring was continued for 1 h at 0-5 C, and the mixture was left to stand overnight at room temperature. It was then poured into ice and dil HCl, and extracted with Et2O. The Et2O solution was washed successively with water, NaHCO3 solution, and brine, dried (MgSO4), and concentrated in vacuo. The residue (10.9 g) was chromatographed over SiO2 (70 g). Elution with hexane gave 1.0 g of hydrocarbons, and further elution with hexane/EtOAc (20:1) afforded 6.42 g (74%) of (9RS,12S)-8 as a colorless oil.

The synthetic route of 2695-48-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mori, Kenji; Akasaka, Kazuaki; Matsunaga, Shigeki; Tetrahedron; vol. 70; 2; (2014); p. 392 – 401;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 766-81-4, name is 3-Bromophenylacetylene, 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 766-81-4, Recommanded Product: 766-81-4

(1) by o-methyl nitrobenzene,Zinc powder, acetic acid, water, sodium nitrite, sodium azide, m-bromophenylacetylene, cuprous iodide,The molar ratio of sodium ascorbate to dimethyl sulfoxide is 1: 5: 10: 20: 1: 4: 1: 0.02: 0.1: 70,First1mmol o-nitrobenzene, 5mmol zinc powder, 10mmol acetic acid,20mmol water was added to the reactor, the reaction at room temperature for 9 hours,Subsequently, 1 mmol of sodium nitrite was added to the reactor under an ice-water bath and the reaction was continued for 10 minutes,Then 4mmol sodium azide was added and the reaction was continued for 1 hour,Finally, to the system by adding 1mmol of bromophenyl acetylene,0.02 mmol copper iodide, 0.1 mmol sodium ascorbate,70mmol dimethyl sulfoxide, the reaction 2 hours to obtain the mixed product; (2) Step (1) The resulting mixed product was diluted with 40 mL of water,Then extracted with 400mmol ethyl acetate twice,The extracts were combined and then washed with water and saturated brine each 10mL,Then dried with 2 g of anhydrous sodium sulfate,Under the conditions of a temperature of 35 C and a pressure of 0.03 MPa, the solvent was distilled off under reduced pressure to obtain a crude product,The crude product was further purified by column chromatography (300 mesh silica gel) using ethyl acetate / petroleum ether (ethyl acetate to petroleum ether 1:20 by volume) eluate to give 270 mg of product, yield 86% , The reaction equation is as follows:

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; Kunming University of Science and Technology; Jiang Yubo; Chen Zhen; Zhao Fen; Yang Rui; Xie Kai; Cheng Huiling; (10 pag.)CN104945339; (2017); B;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 1647-26-3, A common heterocyclic compound, 1647-26-3, name is 1-Bromo-2-cyclohexylethane, molecular formula is C8H15Br, 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.

Example 201 (R)-2-Ethyl-piperazine-1-carboxylic acid 5-(2-cyclohexyl-ethoxy)-2-fluoro-benzyl ester hydrochloride According to example 187 the title compound was synthesised from (R)-2-Ethyl-piperazine-1,4-dicarboxylic acid 4-tert-butyl ester 1-(2-fluoro-5-hydroxy-benzyl)ester and 2-cyclohexyl-ethyl bromide. MS (ISP): 393 (M+H)+.

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

Reference:
Patent; Adams, David Reginald; Bentley, Jonathan Mark; Davidson, James Edward Paul; Dawson, Claire Elizabeth; George, Ashley Roger; Mansell, Howard Langham; Mattei, Patrizio; Mizrahi, Jacques; Nettekoven, Matthias Heinrich; Pratt, Robert Mark; Roever, Stephan; Roffey, Jonathan Richard Anthony; Specklin, Jean-Luc; Stalder, Henri; Wilkinson, Kerry; US2002/143020; (2002); A1;,
Bromide – Wikipedia,
bromide – Wiktionary