Tag: M.W=100-200

55289-36-6, 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. 55289-36-6, name is 3-Bromo-2-methylaniline, This compound has unique chemical properties. The synthetic route is as follows.

A suspension of 7g1 (Alfa, 10 g, 54 mmol) in a mixture of concentrated sulfuric acid (130 mL), water (125 mL), and crushed ice (90 g) is stirred in an ice bath. Sodium nitrite solution in water (26 mL) is added dropwise while maintaining the temperature between 0 and 5C. After the addition is complete, the mixture is stirred for 30 min at the same temperature. The mixture is poured into heated (120C) sulfuric acid (100 mL) and water (75 mL) and the heating is continued for 20 min. The cooled reaction mixture is extracted with Et20. The combined extracts are washed with water, brine, dried over MgS04, filtered and concentrated under vacuum to give compound 7g2.

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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; SIMONEAU, Bruno; DEROY, Patrick; FADER, Lee; FAUCHER, Anne-Marie; GAGNON, Alexandre; GRAND-MAITRE, Chantal; KAWAI, Steven; LANDRY, Serge; MERCIER, Jean-Francois; RANCOURT, Jean; WO2011/100838; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

38573-88-5, name is 1-Bromo-2,3-difluorobenzene, 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. 38573-88-5

General procedure: To an oven-dried 25 mL Schlenk tube containing a stirring bar was added 4.5 mg Pd(OAc)2 (0.02 mmol), 15.7mg nBuPAd2 (0.44 mmol), 2-bromofluorobenzene (0.50 mmol), salicylaldehyde (0.50 mmol), potassium carbonate (1.0 mmol). The Schlenk tube was vacuumed and then purged with argon before DMF (2.0 mL) was injected using a syringe. Afterwards the Schlenk tube in the ice bath was degassed by evacuation and back fillingwith argon three times. The reaction mixture was then stirred for 12 h at 120 ¡ãC. After the reaction was complete,the reaction mixture was diluted with water (5 mL), extracted with ethyl acetate (3 x 10 mL) and dried withanhydrous Na2SO4. After filtration and addition of silica gel into the solution, the organic solvent was reduced evaporated. The crude product was purified by column chromatography using ethyl acetate/n-pentane.

Statistics shows that 38573-88-5 is playing an increasingly important role. we look forward to future research findings about 1-Bromo-2,3-difluorobenzene.

Reference:
Article; Shen, Chaoren; Wu, Xiao-Feng; Synlett; vol. 27; 8; (2016); p. 1269 – 1273;,
Bromide – Wikipedia,
bromide – Wiktionary

55289-36-6, Adding some certain compound to certain chemical reactions, such as: 55289-36-6, name is 3-Bromo-2-methylaniline, 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 55289-36-6.

Intermediate 33D: N-(3-Bromo-2-methylphenyl)-2-(3-chloropyridin-2-yl)acetamide A mixture of sodium 2-(3-chloropyridin-2-yl)acetate (7.39 g, 38 mmol), 3-bromo-2-methylaniline (4.7 mL, 38.4 mmol), DIEA (13.3 mL, 76 mmol) and HATU (14.6 g, 38.4 mmol) in DMF (127 mL) was stirred at room temperature. After 90 min the mixture was diluted with EtOAc and washed twice with 10% LiCl, then with brine. The combined aqueous layers were extracted with EtOAc, and the combined organic phases were dried and concentrated to a small volume. The solution was seeded with a crystal from an earlier batch and allowed to stand overnight to provide a precipitate which was collected by filtration and washed with 50% EtOAc-hexanes to provide a white solid. The filtrate was concentrated and recrystallized similarly three times to provide additional solid. The solids were combined to give N-(3-bromo-2-methylphenyl)-2-(3-chloropyridin-2-yl)acetamide as a white solid (11.43 g, 89% yield). Mass spectrum m/z 339, 341 (M+H)+. 1H NMR (400 MHz, chloroform-d) delta 9.76 (br. s., 1H), 8.52 (d, J=3.5 Hz, 1H), 7.92 (d, J=7.9 Hz, 1H), 7.80 (dd, J=8.1, 1.1 Hz, 1H), 7.36 (d, J=7.9 Hz, 1H), 7.32-7.23 (m, 1H), 7.06 (t, J=8.0 Hz, 1H), 4.16 (s, 2H), 2.39 (s, 3H).

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 55289-36-6.

Reference:
Patent; Batt, Douglas G.; Bertrand, Myra Beaudoin; Delucca, George; Galella, Michael A.; Ko, Soo Sung; Langevine, Charles M.; Liu, Qingjie; Shi, Qing; Srivastava, Anurag S.; Tino, Joseph A.; Watterson, Scott Hunter; US2014/378475; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 583-70-0, name is 2,4-Dimethylbromobenzene, 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 583-70-0, 583-70-0

to a suspension of magnesium powder (239 mg, 9.79 mmol) in dry THF (small amount) was added dropwise 1 -bromo-2,4-dimethylbenzene (1.64 g, 8.86 mmol) diluted in dry THF (20 mL) and the reaction was heated at 40C. After completion of Grignard reagent, 2-methyl-N-[(5-methylfuran-2- yl)methylidene]propane-2-sulfinamide Ex.19a (995 mg, 4.66 mmol) diluted in THF (10 mL) was added to the solution. The reaction mixture was stirred at rt overnight. Water was added to quench the reaction. The two layers were partitionated and the organic layer was dried over Mg504, filtered and the solution was concentrated under reduced pressure. The crude material was purified by silica gel column chromatography using a gradient of hexanes/EtOAc ([5:11 to [4:1]) to afford N-[(2,4-di methyl phenyl)(5-methylfuran-2-yl)methyl]-2- methylpropane-2-sulfinamide (1 .27 g, 85%) as yellowish oil

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, 2,4-Dimethylbromobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GENFIT; DELHOMEL, Jean-Francois; PERSPICACE, Enrico; MAJD, Zouher; PARROCHE, Peggy; WALCZAK, Robert; (284 pag.)WO2018/138362; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

586-61-8, 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 586-61-8 as follows.

5-cyano-2-fluorobenzeneboronic acid pinacol ester (1.98 g, 8.0 mmol) and 4-bromoisopropylbenzene (2.39 g, 12 mmol) were dissolved in 20 ml of dioxane, and Pd(PPh3)4 was added. (924 mg, 0.8 mmol) and CsCO3 (5.2 g, 16.0 mmol) were reacted at 90 C overnight under nitrogen. The reaction liquid was filtered through diatomaceous earth.The filtrate was spin-dried and then subjected to petroleum ether column chromatography to yield 1.35 g of colorless oily liquid, yield: 70.6%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 586-61-8, and friends who are interested can also refer to it.

Reference:
Patent; China Pharmaceutical University; You Qidong; Xu Xiaoli; Jiang Fen; Guo Anping; Xu Jiachen; (26 pag.)CN108147978; (2018); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 615-36-1, name is 2-Bromoaniline, molecular formula is C6H6BrN, 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. 615-36-1

General procedure: Compound 2b-l were synthesized according to the reported method:1A mixture of aniline (10 mmol), iodoalkane (22 mmol) and K2CO3(22mmol) in DMF (80 mL) was refluxed at 75 C. After completion of thereaction monitored by TLC, the mixture was poured into aqueous NaHCO3solution and extracted with ethyl acetate. The organic layer was washed with brine,dried over sodium sulfate and concentrated in vacuo. Purification by columnchromatography on silica gel produced N,N-dimethylanilines 2b-l.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 615-36-1, its application will become more common.

Reference:
Article; Shen, Hang; Zhang, Xiaohui; Liu, Qing; Pan, Jing; Hu, Wen; Xiong, Yan; Zhu, Xiangming; Tetrahedron Letters; vol. 56; 41; (2015); p. 5628 – 5631;,
Bromide – Wikipedia,
bromide – Wiktionary

3814-30-0, Adding a certain compound to certain chemical reactions, such as: 3814-30-0, name is (Bromomethyl)cyclopentane, 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 3814-30-0.

39) N-(3-(cyclopentylmethoxy)-2-methoxybenzyl)-3-cyclopropyl-1-methyl-1H-pyrazole-5-carboxamide To a solution of aldehyde (10.0 g, 65.79 mmol, 1.0 eq) in toluene (100 mL) was added 2,4-dimethoxybenzyl amine (10.89 g, 65.79 mmol, 1.0 eq) and the reaction mixture was stirred at room temperature for 24 h. Toluene was removed to give a residue, which was taken in MeOH (100 mL) and then NaBH4 (4.97 g, 131.58 mmol, 2.0 eq) was added slowly. The reaction mixture was stirred at room temperature for 6 h. Solvent was removed and the residue was extracted in Ethyl acetate and stirred with saturated aq NaHCO3 for 1 h. The organic layer was collected, dried and solvent was removed to give the crude amine, which was used in the next step without further purification. To a solution of the crude amine (7.26 mmol, 1.0 eq) in DMF (20 mL) was added the acid (1.21 g, 7.26 mmol, 1.0 eq), DIEA (4.68 g, 36.30 mmol, 5 eq) and HBTU (3.30 g, 8.71 mmol, 1.2 eq) and the reaction mixture was stirred at rt for 12 h. The reaction mixture was then diluted with ethyl acetate (100 mL) and washed with 10% aq HCl (1*50 mL), sat NaHCO3 (1*50 mL) and water (4*50 mL). Organic layer was collected, dried (MgSO4) and evaporated to give a crude product, which was taken in 150 mL of methanol and NaOH (290 mg, 7.26 mmol, 1.0 eq) was added and stirred at room temperature for 24 h. Methanol was removed and the residue was neutralized with 10% aq HCl. The reaction mixture was then extracted with ethyl acetate (2*). Organic layer was collected, dried (MgSO4) and evaporated to give a crude product, which was purified by column chromatography (EtOAc/Hexane) to give the amide. To a solution of the hydroxy amide (500 mg, 1.07 mmol, 1.0 eq) in DMF (15 mL) was added Cs2CO3 (1.04 g, 3.21 mmol, 3.0 eq) and stirred at room temperature for 20 min. Then bromide (261 mg, 1.60 mmol, 1.5 eq) was added and stirred at rt for 24 h. The reaction mixture was then diluted with ethyl acetate (25 mL) and washed with water (4*). Organic layer was collected, dried (MgSO4) and evaporated to give a residue, which was then treated with 95% TFA:H2O for 12 h. TFA was removed and azeotroped with toluene to give a residue, which was purified by column chromatography (EtOAc/Hexane 10% to 50%) to give the desired product. Mass Spectrum (LCMS, ESI Pos.) Calcd. For C12H30N2O3: 384.0 (M+H), Found 362.0.

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, (Bromomethyl)cyclopentane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Prosetta Antiviral ,Inc.; Selvarajah, Suganya; Paulvannan, Kumar; (58 pag.)US2018/118679; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

1073-39-8, 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 1073-39-8 as follows.

To a mixture of 3-bromobicyclo[4.2.0]octa-1,3,5-triene (569 mg, 3.1 1 mmol, 1.00 equiv) in THF (12 mL) was added n-BuLi (2.5M in hexane, 1.30 mL, 1.05 equiv) dropwise at -78C, and the mixture was stirred at -78C for 30 min. 4-(Benzyloxy)-5-bromo-2-methoxybenzaldehyde (1 g, 3.1 1 mmol, 1.00 equiv) in THF (3 mL) was then added to the solution. The reaction mixture was stirred at -78C for 2 h. NH4CI/H20 was added and the mixture was extracted with EtOAc thrice. The combined extracts were washed with brine and dried over Na2S04, then concentrated and purified by chromatography on silica gel (5:1 PE/EA) to yield 1 (4-(benzyloxy)-5-bromo-2-methoxyphenyl)(1,2- dihydrocyclobutabenzen-4-yl)methanol as a light yellow oil. MS (ES) m/z: 409.0 [M-OH]+

According to the analysis of related databases, 3-Bromobicyclo[4.2.0]octa-1,3,5-triene, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; GAUL, Micheal; KUO, Gee-Hong; XU, Guozhang; LIANG, Yin; (218 pag.)WO2018/89449; (2018); 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. 3814-30-0, name is (Bromomethyl)cyclopentane belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 3814-30-0

To a solution of 20.6 g (0.1 mol) of 4-(3,5-difluorophenyl)phenol in 200 mL of N,N-dimethylformamide in a 500 mL of three-necked flask, 4.8 g (0.12 mol) of 60% sodium hydride was added portionwise under nitrogen with stirring at 30 C., and then 16.3 g (0.1 mol) of cyclopentyl methyl bromide was added dropwise. After the reaction was stuffed for 20 hours, it was poured into 500 mL of water, and was extracted with hot petroleum ether (200 mL¡Á2). The combined organic phases was washed with water to neutral, and the solvent was then distilled off under reduced pressure. 15 g of 4-a as white crystals was obtained by recrystallization from ethanol. GC purity: 98.9%.

The synthetic route of 3814-30-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO., LTD.; Yuan, Guoliang; Liang, Zhian; Wang, Kui; Hua, Ruimao; Wen, Gang; Zhang, Miaofang; Meng, Jinsong; (28 pag.)US9303208; (2016); B2;,
Bromide – Wikipedia,
bromide – Wiktionary

111721-75-6,Some common heterocyclic compound, 111721-75-6, name is 2-Bromo-3-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.

Examples 14 and 15 2-({4-[(2,3-Dihydro[l,4]dioxino[2,3-c]pyridin-7- ylmethyl)amino]-l-piperidinyl}methyl)-9-fluoro-l,2-dihydro-4H-pyrrolo[3,2,l- iy]quinolin-4-one hydrochloride, Enantiomers 1 and 2,(a) N-(2-Bromo-3 -fluorophenyl)-3 -phenyl-2-propenamide; To a solution of 2-bromo-3-fiuoroaniline (5.29g, 27.8mmol) in acetone (12ml) was added potassium carbonate (5.75g, 41.8mmol) followed by water (15ml) and the stirred mixture cooled to 00C. Cinnamoyl chloride (4.63g, 27.8mmol) was added portionwise over 15min then the mixture stirred for a further 2h. After this time the reaction mixture was poured onto ice/water and the resulting precipitate collected and dried to yield a white solid (8.Ig). LC-MS: m/z 320/322 (MH)+.

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

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/3690; (2008); A1;,
Bromide – Wikipedia,
bromide – Wiktionary