Month: May 2021

Reference 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.

1,4-dibromo-2,5-dihexyl benzene (8.05 mmoles, 3.255 g), boronic ester 7 (17.7 mmoles, 7.545 g), Na2CO3 (40.3 mmoles, 4.268 g) and Aliquat 336 (0.500 g) were suspended in toluene (100 mL) in a 250 mL two-necked-round-bottom-flask with stir bar and condenser. Reaction mixture degassed for 30 minutes. Pd(PPh3)4 (0.403 mmoles, 0.465 g) added as a powder to reaction mixture. Reaction mixture degassed for a further 15 minutes, whilst simultaneously degassing water (50 mL). Water added via syringe to reaction vessel. Reaction heated to 90 C. for two days. Resulting reaction mixture diluted with ethyl acetate (150 mL), washed with ethyl acetate (3×100 mL). Organic layer washed with brine (2×100 mL), dried over magnesium sulfate, filtered and concentrated. Purification by column chromatography on silica gel using 1:3 dichloromethane: Hexanes to yield white powder (56%, 3.8 g). 1H NMR (500 MHz, CD2Cl2) delta=7.45 (d, J=8.5 Hz, 4H), 7.33-7.31 (m, 5H), 7.26-7.19 (m, 5H), 6.65 (s, 2H), 2.71-2.63 (m, 9H), 1.54 (s, 18H), 1.31-1.20 (m, 14H), 1.15 (t, J=7.49, 7H), 0.83 (t, J=6.85 Hz, 6H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,4-Dibromo-2,5-dihexylbenzene, its application will become more common.

Reference:
Patent; E.I DU PONT DE NEMOURS AND COMPANY; US2012/65432; (2012); 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. 28148-04-1, name is 1,3-Dibromo-2-methylpropane, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 28148-04-1

(a) 1,3-Dimethylphosphetane borane I-73 Prepared according to a procedure similar to that described for 1-ethylphosphetane borane I-64 starting from dimethyl methylphosphonate I-59 (1.2 g, 9.4 mmol) and 1,3- dibromo-2-methylpropane (2.1 g, 9.4 mmol) to provide the title compound as a colourless oil (274 mg, 2.4 mmol, 25%) which was isolated as an ca. 1 :1 mixture of cis/trans isomers.

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 28148-04-1.

Reference:
Patent; AUSPHERIX LIMITED; KING, Nigel Paul; POWELL, Jonathan Raymond; NEGOITA-GIRAS, Gabriel; WATTS, Joseph Michael; ALVAREZ, Alicia Galvan; GUETZOYAN, Lucie Juliette; FREEM, Joshua Robert; CLARKE, Philip Graham; NAYLOR, Alan; (264 pag.)WO2018/220171; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 959992-62-2, name is 6-Bromo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine, 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 959992-62-2, category: bromides-buliding-blocks

Compound 23.1 (320 mg, 1.49 mmol) And sodium hydrogen (179mg, 4.48mmol, 60%) The tetrahydrofuran (20 mL) solution was heated to reflux for 2 hours. Further, allyl chloroformate (540 mg, 4.48 mmol) was added to the above reaction system. The resulting reaction solution was further heated to reflux for 16 hours. Pour the reaction solution into the water. Extracted with ethyl acetate, The organic phase was separated and dried over anhydrous sodium sulfate. filter, concentrate, The residue was purified by prep-TLC ( petroleum ether / ethyl acetate = 1 / 1) to afford compound 23.4 (440 mg, yield: 67%) It is a colorless liquid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Bromo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine, and friends who are interested can also refer to it.

Reference:
Patent; Shanghai Dinuo Pharmaceutical Technology Co., Ltd.; Zhao Zhiming; Gao Daxin; Chen Shoujun; Wu Zhiheng; (105 pag.)CN108623615; (2018); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 716320-92-2,Some common heterocyclic compound, 716320-92-2, name is 5,6-Dibromo-1H-benzo[d][1,2,3]triazole, molecular formula is C6H3Br2N3, 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 solution of IPrAuCl (6.2 mg, 0.01 mmol) and AgNTf2 (4 mg, 0.01 mmol) in 1,2-dichloroethane (3 mL), was added o-alkynylarylazide 1a (43.8 mg, 0.2 mmol) and benzotriazole 2a (95 mg, 0.8 mmol) stepwisely at rt. The reaction mixture was stirred at 80 C with TLC monitoring until complete consumption of the starting material 1a (48 h). Concentration of the reaction mixture, followed by purification through flash chromatography (petroleum/EtOAc = 5/1 as the eluent) afforded 3a (38 mg) and 3a (8.5 mg) as two yellow solid products (75 % total yield, 3a/3a=4.5/1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5,6-Dibromo-1H-benzo[d][1,2,3]triazole, its application will become more common.

Reference:
Article; Chen, Bai-Ling; Chen, Zili; Li, Tao; Zhu, Li-Li; Tetrahedron Letters; (2020);,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 69902-83-6, 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. 69902-83-6, name is 1-Bromo-2-methyl-3-(trifluoromethyl)benzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of l-bromo-2-methyl-3-(trifluoromethyl)benzene (i-4a) (2 g, 8.36 mmol) in CCI4 (20 mL) was added NBS (1.49 g, 8.36 mmol), dibenzoyl peroxide (20 mg, 0.08 mmol). The mixture was stirred under nitrogen at 100 C for 16 h. The solvent was removed in vacuo, and the residue was partitioned between water (15 mL) and DCM (15 mL). The water layer was extracted with DCM (15 mL x 3). The combined organic layers were dried over anhydrous Na2S04 and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (PE/EtOAc = 50/1) to afford the title compound (1.16 g, purity 80%, yield: 43%). LCMS (ESI) calc’d for C8H5Br2F3 [M+H]+: 317, found: 317.

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-Bromo-2-methyl-3-(trifluoromethyl)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BARR, Kenneth Jay; BEINSTOCK, Corey; MACLEAN, John; ZHANG, Hongjun; BERESIS, Richard Thomas; WO2014/28591; (2014); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 35354-37-1, 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 35354-37-1 as follows.

Example 148 (+-)-trans-3,4-Dimethyl-N-(5-methylhexyl)-4-(3-n-propanesulfonylaminophenyl)piperidine To a solution of (+-)-trans-3,4-dimethyl-4-(3-n-propanesulfonylaminophenyl)piperidine (Preparation 40, 220 mg, 0.71 mmol) and 1-bromo-5-methylhexane (140 mg, 0.78 mmol) in N,N-dimethylformamide (7 ml) was added sodium hydrogen carbonate (120 mg, 1.42 mmol) and the resultant mixture was heated overnight at 100° C. The reaction mixture was poured onto water (50 ml) and extracted with diethyl ether (3*50 ml). The combined extracts were washed with brine (50 ml), dried (MgSO4), filtered and concentrated in vacuo to give the crude product which was purified by silica (5 g) chromatography using a gradient solvent system eluding initially with hexane:0.880 ammonia (100:1) then ethyl acetate:hexane:0.880 ammonia (50:50:1) to afford the title compound as a pale yellow oil (77 mg, 27percent). NMR (CDCl3, selected data for the free base): 0.75 (d, 3H), 0.9 (d, 6H), 1.0 (t, 3H), 1.2 (t, 2H), 1.25 (m, 2H), 1.3 (s, 3H), 1.4-1.65 (m, 5H), 1.8 (m, 2H), 2.0 (m, 1H), 2.5 (q, 2H), 2.8 (m, 1H), 3.05 (m, 2H), 7.0-7.3 (m, 4H). MS (APCI): M/Z [MH+] 409.3; C23H40N2O2S+H requires 409.3.

According to the analysis of related databases, 35354-37-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Armer, Richard Edward; Dutton, Christopher James; Gethin, David Morris; Gibson, Stephen Paul; Smith, Julian Duncan; Tommasini, Ivan; US2003/78282; (2003); 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. 21865-50-9, name is 6-Bromo-2,3,4,9-tetrahydro-1H-carbazole, A new synthetic method of this compound is introduced below., Safety of 6-Bromo-2,3,4,9-tetrahydro-1H-carbazole

While purging with nitrogen gas in a 1L round bottom flask at room temperature,6-bromo-1,2,3,4-tetrahydrocarbazole (100 g, 400 mmol),Iodinebenzene (122 g, 600 mmol),Copper iodide (3.80 g, 20.0 mmol),Potassium phosphate (178g, 840mmol),1,2-cyclohexane diamine (91.3 g, 800 mmol),1,4-dioxane (500 mL) was added and refluxed for 12 hours. After TLC confirms the end of the reaction,After cooling the reaction solution to room temperature,Methylene chloride and water were added to separate the layers. The aqueous layer was removed and the organic layer was concentrated under reduced pressure,Purification by silica gel column chromatography gave <1-a>(86.5 g, 265 mmol). (Yield 66.3%)

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; SFC Ltd.; Shin Bong-gi; Kim Si-in; (80 pag.)KR102004386; (2019); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 73908-04-0, 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 73908-04-0 as follows.

General procedure: An oven-dried Schlenk tube containing a stirring bar was charged with NiI2 (2.5-10.0 mol%), L1 (4.4-17.6 mol%) and Mn powder (3 equiv.). The Schlenk tube was then evacuated and back-filled under a CO2 flow (this sequence was repeated three times) and finally an atmospheric pressure of CO2 was established. The corresponding alkyl bromide (0.5 mmol) and DMF (1 M) were added under a CO2 flow. Once added, the Schlenk tube was closed at atmospheric pressure of CO2 (1 atm) and stirred at the desired temperature for 20-48 h. The mixture was then carefully quenched with 2 M HCl to hydrolyse the resulting carboxylate and extracted with EtOAc (three times). The combined organic layer was washed with brine (three times), dried over anhydrous MgSO4, filtrated and evaporated. The resulting crude carboxylic acid was purified by conventional flash chromatography in silica gel using hexanes/EtOAc 3:1 with 1% formic acid.

According to the analysis of related databases, 73908-04-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Julia-Hernandez, Francisco; Moragas, Toni; Cornella, Josep; Martin, Ruben; Nature; vol. 545; 7652; (2017); p. 84 – 88;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 268733-18-2, A common heterocyclic compound, 268733-18-2, name is 4-Bromo-3,5-bis(trifluoromethyl)aniline, molecular formula is C8H4BrF6N, 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.

(1)1.0 g of 3,5-bis(trifluoromethyl)-4-bromoaniline was dissolved in 3 mL of hexamethylphosphoric acid triamide, and 730 mg of copper cyanide was added and reacted at 140C for 8 hours under irradiation with microwaves. The reaction solution was left to cool, and then, to the reaction solution, water and ethyl acetate were added, whereupon an insoluble solid content was removed by filtration through cerite. The organic layer was separated, and the aqueous layer was extracted twice with ethyl acetate. The organic layers were put together and washed with a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=5/2) to obtain 550 mg of 3,5-bis(trifluoromethyl)-4-cyanoaniline as white solid.

The synthetic route of 268733-18-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ISHIHARA SANGYO KAISHA, LTD.; EP2172456; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 41825-73-4, 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. 41825-73-4 name is 2-Bromo-4,6-dimethylaniline, 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.

Production Example 1-40 Production of Compound Represented by Formula (1-41) Production of Compound Represented by Formula 3-1 2.04 g of 1,1?-bis(diphenylphosphino) ferrocene-palladium(II) dichloride-dichloromethane complex, 48.8 g of cesium carbonate, and 10 g of the compound represented by Formula (5-1) were dissolved in 125 ml of N,N-dimethylformamide at room temperature in a nitrogen atmosphere. 32.5 ml (1.0 M hexane solution) of triethylborane was added dropwise to the obtained solution, followed by stirring at room temperature for 16 hours in a nitrogen atmosphere. After the reaction liquid was filtered using Celite (registered trademark), water was added to the filtrate, the resultant product was extracted with tert-butyl methyl ether, and the organic layer was washed with a saturated saline solution, and dried over anhydrous magnesium sulfate. The obtained organic layer was concentrated under reduced pressure, and the resultant product was subjected to silica gel column chromatography (eluent, ethyl acetate_hexane=1:19?1:9), whereby 3.18 g of the compound represented by Formula (3-1) was obtained. 1H NMR (CDCl3) delta ppm: 6.78 (2H, s), 3.49 (2H, s), 2.51 (2H, q), 2.23 (3H, s), 2.16 (3H, s), 1.24 (3H, t)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-4,6-dimethylaniline, and friends who are interested can also refer to it.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; Jin, Yoshinobu; Fujino, Yoshimi; US2015/289505; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary