Month: July 2021

Application of 583-70-0,Some common heterocyclic compound, 583-70-0, name is 2,4-Dimethylbromobenzene, molecular formula is C8H9Br, 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.

Add 2,4-dimethylbromobenzene to a 500 mL three-necked flask equipped with magnetic stirring at room temperature.2,4-Dimethylaniline, Pd2(dba)3, tri-tert-butylphosphine, sodium t-butoxide, toluene.After the addition, the nitrogen gas was replaced 3 times, the stirring was started, and the oil bath was heated and heated to reflux for 5 hours.The TLC tracking reaction showed that the two starting materials were completely reacted (PE/EA = 20:1, product Rf = 0.8) and the reaction was stopped. The reaction solution was cooled to room temperature, stirred for 10 minutes with pure water, separated, and the aqueous phase was extracted with toluene, and the toluene phase was combined and saturated.Washed with brine, dried over anhydrous sodium sulfate, filtered and evaporatedDilute the crude product with as little petroleum ether as possible: dichloromethane = 10:1, and place the liquid on a silica gel column.Keep the polarity of the eluent unchanged with petroleum ether: dichloromethane = 10:1 until the product is rinsed.Dry under reduced pressure to give an off-white solid.Recrystallization from n-hexane gave 13 g of a white crystalline solid.HPLC 99.18%, yield 57%.

The synthetic route of 583-70-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Beijing Dingcai Technology Co., Ltd.; Gu’an Dingcai Technology Co., Ltd.; Gao Wenzheng; Ren Xueyan; (34 pag.)CN109665935; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 174508-31-7, A common heterocyclic compound, 174508-31-7, name is 5,7-Dibromo-2,3-dihydrothieno[3,4-b][1,4]dioxine, molecular formula is C6H4Br2O2S, 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.

To 5,7-dibromo-2,3-dihydrothieno[3,4-b]-1,4-dioxin were added 2.0 equivalents of tert-butyl 4-tributyltin-2,3-dihydro-2-oxo-1H-thieno[3,4-d]imidazole-1-carboxylate obtained in the same manner as described in Example 7, dry 1,4-dioxane in an amount equivalent to 10 ml/mol relative to 5,7-dibromo-2,3-dihydrothieno[3,4-b]-1,4-dioxin, and 0.1 equivalents of trans-dichlorobistriphenylphosphine palladium. Under argon gas atmosphere, a reaction was advanced by refluxing at 120 C. for 40 hours, and then the reaction was stopped by adding an excessive amount of a saturated aqueous ammonium chloride solution. The resulting reaction liquid was filtered while being diluted with ethyl acetate, and to the resulting filtrate was added three-fold volume of a saturated aqueous potassium fluoride solution, followed by stirring for 2 hours. After the removal of the aqueous phase and insoluble matter, the organic layer containing the product was dried over sodium sulfate, then the solvent was distilled off, and the residue was purified by silica gel column chromatography using an ethyl acetate/hexane solvent, so that tert-butyl 4-[7-(2,3-dihydro-2-oxo-1-tert-butoxycarbonyl-1H-thieno[3,4-d]imidazol-4-yl)-2,3-dihydrothieno[3,4-b]-1,4-dioxin-5-yl]-2,3-dihydro-2-oxo-1H-thieno[3,4-d]imidazole-1-carboxylate was obtained.

The synthetic route of 174508-31-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kuraray Co., Ltd.; Kondou, Yoshirou; Nakano, Kirihiro; Otake, Tomiaki; US8519150; (2013); B2;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 117635-21-9,Some common heterocyclic compound, 117635-21-9, name is 1,4-Dibromo-2,5-dihexylbenzene, molecular formula is C18H28Br2, 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 3: In the dry box the mixture of boronic acid pinacol ester,3, (5.8g.16.B2mmol), 1,4-dlbmmo-295-dthexylbenzene(3.4g, 8.4mmol), .Aiiquat 336(0.Bg), and Pd(PP%)4 (0.486g, 0421 mmol) in degassed toluene (lOOmL) was prepared. Outside dry box, the degassed Na2003 (2.87g, 2523mmo1 In 50 mL of water) solution was added to the fomier mixture under nitrogen, and then the resultant mixture was stirred at 90C for 42hrs. Theorganic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined orgqnlc layers were dried over anhydrous MgSO4. Filtration, concentration & the filtrate, and then the silica column chromatography (0-3% ethyl acetae in hexane) provided the desired product (2Mg, 8% yield) as a viscous liquid

The synthetic route of 117635-21-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; RADU, Nora Sabina; FENNIMORE, Adam; WO2015/89027; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

74586-53-1, name is 3-Bromo-5-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. Application In Synthesis of 3-Bromo-5-methylaniline

Intermediate 5 N-(3-Bromophenyl)cyclohexanecarboxamide [00398] Cyclohexanecarbonyl chloride (61.4 g, 419 mmol) was added to a solution of 3- bromoaniline (60 g, 349 mmol), DMAP (4.26 g, 34.9 mmol), TEA (70.6 g, 698 mmol) in DCM (400 mL) at 0 C. The mixture was slowly warmed to 15 C and stirred for 14 h. Water (200 mL) was added, and the mixture was extracted with DCM (3 x300 mL). The combined organic phases were washed with brine (2×300 mL), dried over anhydrous Na2S04, filtered and concentrated. The residue was purified by recrystallization from MTBE (200 mL) to give N-(3- bromophenyl)cyclohexanecarboxamide (90 g, 85%) as a red brown solid. MS: 282.1 [M+H]+. The Intermediates below were synthesized from the appropriate amines following the procedure described for Intermediate 5. Note: DMAP was not used for the above Intermediates; reaction time: 2-16 h. *Acetonitrile was used as a solvent instead of DCM.

The synthetic route of 74586-53-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; METACRINE, INC.; SMITH, Nicholas D.; GOVEK, Steven P.; NAGASAWA, Johnny Y.; (228 pag.)WO2017/49172; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 7745-91-7, These common heterocyclic compound, 7745-91-7, name is 3-Bromo-4-methylaniline, 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.

General procedure: To a well stirred solution of compound 6a or 6b (0.2 g, 1 Eq.) in absolute ethanol (10 mL), the appropriately substituted anilines(1.1 Eq) was added and the reaction mixture was refluxed for 2-3 h until TLC showed full consumption of starting materials. The excess of solvent was evaporated under reduced pressure to yield the crude solids, which were further purified by recrystallization with methanol to afford the desired title compounds (7-43).

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

Reference:
Article; Cherukupalli, Srinivasulu; Chandrasekaran, Balakumar; Kry?tof, Vladimir; Aleti, Rajeshwar Reddy; Sayyad, Nisar; Merugu, Srinivas Reddy; Kushwaha, Narva Deshwar; Karpoormath, Rajshekhar; Bioorganic Chemistry; vol. 79; (2018); p. 46 – 59;,
Bromide – Wikipedia,
bromide – Wiktionary

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 25017-13-4 as follows. Application In Synthesis of 1-(2-Bromoethyl)-3-fluorobenzene

Example 5 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 (2×20 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, 1H), 7.03-6.93 (m, 3H), 2.96 (t, J=7.4 Hz, 2H), 2.63 (t, J=7.4 Hz, 2H)

According to the analysis of related databases, 25017-13-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Silverman, Richard B.; Cinelli, Maris A.; US2015/210644; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 4333-56-6, The chemical industry reduces the impact on the environment during synthesis 4333-56-6, name is Bromocyclopropane, I believe this compound will play a more active role in future production and life.

[000225j To a solution of Compound El (20 g, 96 mmol) in 1 -methyl-2-pyrrolidinone(300 mL) was added cesium carbonate (62.8 g, 193 mmol) and bromocyclopropane (24 mL,289 mmol). The mixture was stirred for 24 h while keeping the inner temperature between145 C and 155 C. After the reaction was cooled to ambient temperature, the dark solutionwas diluted with water (400 mL) and extracted with a mixture of ethyl acetate in petroleumether (15% v/v) (300 mL x 3). The combined organic phases were washed with brine (150mL x 4), dried over anhydrous sodium sulfate, filtered, and concentrated to afford the crude product. The crude product was purified with flash column chromatography on silica gel (petroleum ether) to furnish Compound E2. HPLC: Rt: 1.96 minute. ?H-NMR (CDC13, 400 MHz): 5 (ppm) 0.80-0.88 (m, 4H), 3.67-3.82 (m, 1H), 7.15 (d, J 8.8 Hz, 1H), 7.32 (dd, J 8.8, 2.4 Hz, 1H), 7.47 (d, J 2.4 Hz, 1H).

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, Bromocyclopropane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BIOMARIN PHARMACEUTICAL INC.; WANG, Bing; WO2015/65937; (2015); 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. 67567-26-4, name is 4-Bromo-2,6-difluoroaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 4-Bromo-2,6-difluoroaniline

General procedure: The starting materials 1 and 2 were commercially available (Energy Chemical, Shanghai, China).Compound 2 (3.72 mmol) was added to a stirred solution of compound 1 (3.38 mmol) in glacial aceticacid (10 mL). The reaction mixture was then stirred at 110 C for 4 h. After completion of the reaction,the solvent was evaporated, and the residue was purified on a silica gel column chromatography andeluted with ethyl acetate/petroleum ether (bp 60-90 C) (1:3, v/v) to give compounds 3.

The synthetic route of 67567-26-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gao, Wei; Li, Xiaotian; Ren, Da; Sun, Susu; Huo, Jingqian; Wang, Yanen; Chen, Lai; Zhang, Jinlin; Molecules; vol. 24; 23; (2019);,
Bromide – Wikipedia,
bromide – Wiktionary

1073-39-8, name is 3-Bromobicyclo[4.2.0]octa-1,3,5-triene, 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. Safety of 3-Bromobicyclo[4.2.0]octa-1,3,5-triene

To a mixture of 3-bromobicyclo[4.2.0]octa-1,3,5-triene (309.3 mg, 1.69 mmol, 1.20 equiv) in tetrahydrofuran (12 mL) was added n-BuLi (0.68 mL, 1.20 equiv, 2.5 M in hexane) dropwise at -78C. The solution was stirred for 30 min at -78C. To the resulting mixture was then added a solution of 5-bromo-2- ethylbenzaldehyde (300 mg, 1.41 mmol, 1.00 equiv) in tetrahydrofuran (3 mL) dropwise at -78C. The reaction mixture was stirred for 2 h at -78C. NH4CI/H20 was added and the mixture was extracted with ethyl acetate three times. The combined extracts were washed with brine and dried over Na2S04, then concentrated and purified by chromatography on silica gel (1 :5 EA/PE) to yield bicyclo[4.2.0]octa-1 (6),2,4-trien-3-yl(5-bromo-2-ethylphenyl)methanol as a yellow oil. MS (ES) m/z: 299.0, 301.0[M-OH]+.

The synthetic route of 1073-39-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; GAUL, Micheal; KUO, Gee-Hong; XU, Guozhang; LIANG, Yin; (218 pag.)WO2018/89449; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 34950-82-8, A common heterocyclic compound, 34950-82-8, name is 7-Bromo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine, molecular formula is C7H7BrN2O, 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.

To a microwave vial is added R-8 (100 mg, 0.47 mmol), R-9 (44 mg, 0.047 mmol), HP(t-13u)3—-13F4 (27 mg, 0.093 mmol), Mo(CO)5 (123 mg, 0.47 mmol) and piperidine (0.14 mE, 1.4 mmol). Contents are dissolved in dioxane (3 mE) then treated with DI3U (0.14 mE, 0.93 mmol) and DIEA (0.33 mE, 1.86 mmol) and heated at 150 C. in the microwave for 30 mm. The mixture is cooled to ambient temperature then filtered through a pad of Celite, concentrated and purified by RHPEC to give Ex 3 (35 mg, 30%).

The synthetic route of 34950-82-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boehringer Ingelheim International GmbH; BOSANAC, Todd; BURKE, Michael J.; COOK, Brian Nicholas; DISALVO, Darren Todd; KIRRANE, JR., Thomas Martin; SHEN, Yue; US2018/354968; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary