Month: March 2021

7745-91-7, name is 3-Bromo-4-methylaniline, 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. category: bromides-buliding-blocks

The solution of 4-methoxy-1,3-benzenedichloride (6)(0.93 g, 4.0 mmol) in anhydrous THF (15 mL) was added to3-bromine-4-methylaniline (1.48 g, 8.0 mmol). This solutionwas stirred rapidly at room temperature for about 1 hand then pyridine (1 mL) was added. The solution wasrefluxed for 4-8 h. The residue was recrystallized frommethanol-water to terminal compound 1a (1.81 g, yield85.2%). The other compounds (1b-1i) were prepared with thesimilar method of preparing compound 1a. White solid (The residue was recrystallized by 50%ethanol.); Yield = 85.2%; Rf: 0.38; m.p.: 157.2-158.4 C;IR (KBr) upsilonmax 3340.21, 2971.89, 1665.12, 1601.07,1447.33, 1267.97, 982.92, 758.72 cm-1; 1H-NMR(400 MHz, CDCl3, TMS): delta = 10.06 (s, 2H, 2¡Á -CONH-),8.72 (s, 1H, Ar-2-H), 8.62 (d, J = 6.8 Hz, 1H, Ar-6-H), 8.42(d, J = 7.2 Hz, 1H, Ar-5-H), 8.15 (s, 2H, Ar-2?,2?-H), 7.86(d, J = 4.8 Hz, 2H, Ar-6?, 6?-H), 7.49 (d, J = 7.8 Hz, 2H,Ar-5?, 5?-H), 3.78 (s, 3H, Ar-4-OCH3), 1.43 (s, 6H, Ar-4?,4?-CH3); 13C-NMR (101 MHz, CDCl3): delta = 164.49 (C, C= O), 163.42 (C, C = O), 142.57 (C, Ar-4-C), 141.97 (C,Ar-1?-C), 139.68 (C, Ar-1?-C), 133.63 (C, Ar-1-C), 133.13(C, Ar-3-C), 132.29 (C, Ar-3?-C), 131.26 (C, Ar-3?-C),130.28 (CH, Ar-2-C), 128.92 (CH, Ar-6-C), 127.83 (CH,Ar-5-C), 126.23 (CH, Ar-2?-C), 124.63 (CH, Ar-2?-C),122.65 (CH, Ar-5?-C), 121.31 (CH, Ar-5?-C), 118.91 (CH,Ar-6?-C), 117.79 (CH, Ar-6?-C), 116.46 (C, Ar-4?-C), 115.36 (C, Ar-4?-C), 63.49 (O-CH3, Ar-4-O-CH3), 14.76(2¡Á CH3, Ar-4?,4?-CH3); MS (m/z): 532.9820 [M + H]+.

The synthetic route of 7745-91-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chen, Guangling; Wang, Chaoqing; Zhang, Zhihao; Liu, Xiujie; Medicinal Chemistry Research; vol. 28; 9; (2019); p. 1413 – 1424;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 100189-84-2, A common heterocyclic compound, 100189-84-2, name is 2,5-Dibromo-1,3-dimethylbenzene, molecular formula is C8H8Br2, 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.

In a 25 mL Schlenk tube, 200 mg of 2,5-dihexyldioctyl-3,6-bisthiophenepyrrole [3,4-c]-pyrrole-1,4-dione was added according to a 2:1 molar ratio. Monomer 1), 35.2 mg of 2,6-dimethyl-1,4-dibromobenzene (monomer 4), sequentially added 200 mg of cesium carbonate, 8 mg of pivalic acid, 4 mg of Pd2(dba)3 catalyst, 3.3 mg of P ( o-MeOPh) 3 ligand. The moles of the catalyst Pd2(dba)3, the ligand P(o-MeOPh)3, the promoter pivalic acid PivOH, and the base Cs2CO3 were 1.5%, 3%, 30%, and 200%, respectively, of the monomer 1. In 6 mL of anhydrous toluene, the mixture was stirred under an inert atmosphere and heated to 120 C for 46 h. The obtained crude product was separated by silica gel column chromatography, and different conjugate length oligomers were collected, and the obtained solid product was vacuum dried under a rotary evaporator to obtain three conjugated oligomers of increasing degree of polymerization. , O8 and O9.The yields of O7, O8 and O9 are 35%, 30% and 25%, respectively.

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; Jiangxi University of Science and Technology; Liu Shiyong; Shen Zhaoqi; Liu Hui; Liu Lilin; Wen Herui; (20 pag.)CN108752367; (2018); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 39478-78-9, 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. 39478-78-9, name is 5-Bromo-2-methylaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Reference Example 355-Cyclopropyl-2-methylanilineAt room temperature, to a suspension of 5-bromo-2-methylaniline (372 mg), cyclopropylboronic acid monohydrate (270 mg), tricyclohexylphosphine (56.0 mg), and potassium phosphate (1.49 g) in toluene (8.0 mL)-water (0.4 mL) was added palladium (II) acetate (22.4 mg), and the mixture was stirred under an argon gas atmosphere at 100 C. for 6 hours. To the reaction mixture were added water and ethyl acetate, and the organic layer was separated. The aqueous layer was extracted with ethyl acetate and the organic layer was combined. The layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (eluting solvent: hexane-ethyl acetate) to obtain the title compound (256 mg).

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, 5-Bromo-2-methylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; KISSEI PHARMACEUTICAL CO., LTD.; US2012/122931; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 25017-13-4, name is 1-(2-Bromoethyl)-3-fluorobenzene, 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. SDS of cas: 25017-13-4

3-Fluorophenethyl Cyanide (24). 3-Fluorophenethyl bromide (23, 1.00 g, 12.3 mmol) was diluted in dry DMF (25 mL). Sodium cyanide (1.06 g, 61.6 mmol) was added in one portion, and the mixture was heated to 60 C. under argon for 16 h. The mixture was cooled and concentrated, and the residue was partitioned between EtOAc and H2O (50 mL each). The layers were separated, and the aqueous phase was extracted with EtOAc (2¡Á20 mL). The organic layers were washed with H2O and sat. aq. NaCl (50 mL each), dried over anhydrous sodium sulfate, and concentrated. The resulting oil was purified by flash column chromatography (SiO2), eluting with a gradient of 5% EtOAc in hexanes to 30% EtOAc in hexanes to yield the desired product as a colorless oil (0.638 g, 87%). 1H-NMR (500 MHz; CDCl3): delta 7.31 (td, J=7.9, 6.0 Hz, 1 H), 7.03-6.93 (m, 3 H), 2.96 (t, J=7.4 Hz, 2 H), 2.63 (t, J=7.4 Hz, 2 H).

The synthetic route of 1-(2-Bromoethyl)-3-fluorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Northwestern University; Silverman, Richard B.; Cinelli, Maris A.; US9212144; (2015); B2;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 1647-23-0, name is 1-Bromo-3,3-dimethylbutane, 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 1647-23-0, Recommanded Product: 1-Bromo-3,3-dimethylbutane

1-(2-Chloro-phenyl)-4,4-dimethyl-pentan-1-one 14.1 g (580 mmole) Magnesium turnings were placed in a 1 l-roundbottom flask equipped with a dropping funnel and a reflux condenser, and 60 ml of THF were added. The magnesium was etched slightly with a few crystals of iodine and then 2 g of 1-bromo-3,3-dimethyl-butane were added and the mixture was heated locally. After the start of the Grignard-formation the rest of the 1-bromo-3,3-dimethyl-butane in 350 ml of THF (88.1 g in total, 533 mmole) were added within a period of 20 min. The mixture was refluxed for 1.5 h and then cooled to room temperature. In a separate 2 l-roundbottom flask 63.9 g (464 mmole) of 2-chloro-benzonitrile and 141 mg (0.16 mole %) copper(I)iodide were dissolved in 265 ml of THF. The Grignard-solution was added dropwise over a period of 30 min and the reaction mixture was refluxed for 3 h. After standing overnight at room temperature, a mixture of 190 ml water and 127 ml concentrated hydrochloric acid were added very carefully, causing a strongly exothermic reaction. The mixture was stirred at 50 C. for 1 h and the layers were separated. The aqueous layer was extracted twice with 150 ml of toluene each. The combined organic layers were washed twice with 2 M sulphuric acid, once with a saturated sodium bicarbonate solution and once with a saturated sodium chloride solution. After drying over magnesium sulphate the solvent was evaporated in vacuo to yield 103.8 g (quant.) of the desired phenone as slightly brown oil. 1H-NMR (400 MHz, CDCl3): delta=7.41-7.26 (m, 4H, aromatic), 2.87 (m, 2H, COCH2), 1.59 (m, 2H, CH2-t-Bu), 0.90 (s, 9H, t-Bu) ppm.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-3,3-dimethylbutane, and friends who are interested can also refer to it.

Reference:
Patent; Lammus Novolen Technology GmbH; US8299287; (2012); B2;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 153505-37-4, name is 4-Bromo-5-fluorobenzene-1,2-diamine, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 153505-37-4

The compound was synthesized starting from (S)-4-phenyloxazolidin-2-one (1 equiv., 0.328 g, 2 mmol), 4-bromo-5-fluorobenzene-1,2-diamine (1 equiv., 0.412 g, 2 mmol), copper(I) iodide (0.1 equiv., 0.040 g, 0.2 mmol), cesium fluoride (2 equiv., 0.608 g, 4 mmol), cyclohexane-1,2-diamine (0.1 equiv., 0.024 mL, 0.2 mmol). The dried solids were given together in a reaction flask and the flask was purged with argon. A solution of cyclohexane-1,2-diamine in 4 mL dioxane was added to the flask. The reaction was stirred at 95 C. for 48 hours, before the reaction was cooled down to 45 C. and filtered through a pad of CELITE. The pad was washed with warm dichloromethane and the solution was concentrated under reduced pressure. The intermediate product was purified via FPLC using a chloroform-methanol gradient (0?10%, product elutes at about 5%).Yield: 0.078 g (13.6%)

According to the analysis of related databases, 153505-37-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PROBIODRUG AG; US2011/92501; (2011); 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. 5469-19-2, name is 1-Bromo-2,4,5-trimethylbenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 5469-19-2

1-Bromo-2,4,5-trimethylbenzene (25.0 g, 0.125 mol) was dissolved in methylene chloride (500 mL). Aluminum chloride (20.1 g, 0.151 mol) and dichloromethyl methyl ether (13.7 mL, 0.151 mol) were added in a nitrogen atmosphere at -78C. After stirring at -78C for five minutes, water (500 mL) was added, followed by extraction with methylene chloride (400 mL). The organic layer was washed with brine and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate = 25/1) to give the target compound (14.4 g, yield: 51%) as a white solid. 1H-NMR (CDCl3, 400MHz):delta ppm: 2:27 (3H, s), 2.36 (3H, s), 2.55 (3H, s), 7.51 (1H, s), 10.53 (1H, s). MS (EI) m/z: 226 (M+)

The synthetic route of 5469-19-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Daiichi Sankyo Company, Limited; EP1914229; (2008); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 399-94-0,Some common heterocyclic compound, 399-94-0, name is 1-Bromo-2,5-difluorobenzene, molecular formula is C6H3BrF2, 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 2-bromo-1,4-difluorobenzene (5.81 mL, 51.8 mmol) in dry THF (50 mL) was added isopropylmagnesium chloride (2.0 M in THF, 31.1 mL, 62.2 mmol) at -78 C. The mixture was slowly warmed to 0 C., stirred for 1 hour at that temperature and then cooled to -78 C. again. After addition of a solution of tert-butyl 2-oxopyrrolidine-1-carboxylate (11.5 g, 62.2 mmol) in dry THF (20 mL) at -78 C., the reaction mixture was allowed to warm to room temperature with stirring for 2 hours and quenched with saturated aq. NH4Cl. The mixture was extracted with EtOAc twice. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to afford tert-butyl 4-(2,5-difluorophenyl)-4-oxobutylcarbamate (15.5 g, 100%) as a pale green oil, which was used for the next reaction without further purification.

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-2,5-difluorobenzene, its application will become more common.

Reference:
Patent; HANDOK INC.; CMG Pharmaceutical Co., Ltd.; Kim, Moonsoo; Lee, Chaewoon; Lee, Gilnam; Yoon, Cheolhwan; Seo, Jeongbeob; Kim, Jay Hak; Lee, Minwoo; Jeong, Hankyul; Choi, Hyang; Jung, Myung Eun; Lee, Ki Nam; Kim, Hyun Jung; Kim, Hye Kyoung; Lee, Jae Il; Lee, MinWoo; Kim, Misoon; Choi, Soongyu; (124 pag.)US2016/168156; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 52997-43-0, name is 7-(Bromomethyl)pentadecane, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 52997-43-0

To the reaction flask was added 3,6-dibromofluorene (3.24 g, 10.0 mmol)6.7 mL of 1-bromo-2-hexyl decane,0.1 g of tetrabutylammonium iodide (catalyst),10 mL of a 50% aqueous solution of sodium hydroxide and 15 mL of DMSO.And heated to 100 C for 18 hours under nitrogen protection.After the raw material is completely reacted, the reaction will be quenched by adding water,Then washed with water, extracted with petroleum ether,The resulting organic phase was dried over anhydrous magnesium sulfate and filtered,The crude product was concentrated, separated by silica gel column chromatography, and petroleum ether was used as eluent and dried in vacuo to give compound 1,A total of 6.41 g, the yield was 8

According to the analysis of related databases, 52997-43-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wuhan University of Technology; Xiao, Shengqiang; Yang, Mingyan; You, Wei; Zhan, Chun; (11 pag.)CN104557972; (2017); B;,
Bromide – Wikipedia,
bromide – Wiktionary

Application 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.

Example 195 4-[(3-Bromo-4-fluorophenyl)amino]-6-nitro-3-quinolinecarbonitrile A mixture of 3.8g (16.33mmol) of 4-chloro-6-nitro-3-quinolinecarbonitrile and 3.7g (20mmol) of 3-bromo-4-fluoroaniline in 200mL of ethanol was refluxed for 3hr. After the solvent was removed, the residue as dissolved in ethyl acetate and washed with sodium bicarbonate. The product was collected as a pale yellow solid, 6.5g (71%); ESMS m/z 387.3, 389.2, mp 269-270C (dec).

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; Wyeth Holdings Corporation; EP1263503; (2005); B1;,
Bromide – Wikipedia,
bromide – Wiktionary