Month: March 2021

Adding a certain compound to certain chemical reactions, such as: 4333-56-6, name is Bromocyclopropane, 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 4333-56-6, Application In Synthesis of Bromocyclopropane

Dissolve 4-bromo-benzenethiol (2.00 g, 10.6 mmol) in dry DMSO (50 mL) under a nitrogen atmosphere. Add potassium tert-butoxide (1. 30 g, 11.7 mmol) and stir until dissolved. Add cyclopropyl bromide (2.6 mL, 31.8 mmol) and heat the reaction to 80 C for 2 days. Cool to room temperature and pour the reaction into water (500 mL). Extract the aqueous layer with Et20 (2 x 200 mL) and wash the combined organic layers with water (100 mL). Dry over sodium sulfate and concentrate in vacuo. Chromatograph the residue on a Si02 column eluting the material with hexanes to give 1.73 g of 1-bromo-4- cyclopropylsulfanyl-benzene (72%). Dissolve l-bromo-4-cyclopropylsulfanyl-benzene (1.73 g, 7.55 mmol) in dry methylene chloride (75 mL). Slowly add mCPBA (4.8 g, 18. 8 mmol, 68%) in portions to control a mild exotherm. After stirring for 1 hour, filter the resultant precipitate. Wash the filtrate with IN NaOH (50 mL) and dry the organic layer with sodium sulfate. Concentrate in vacuo to yield 2.0 g of 1-bromo-4-cyclopropanesulfonyl-benzene (100%). Dissolve l-bromo-4-cyclopropanesulfonyl-benzene (500 mg, 1.91 mmol), bis (pinacolato) diboron (577 mg, 2.29 mmol), potassium acetate (513 mg, 5.70 mmol) and PdCl2 (dppf) CH2C12 (46 mg, 0.057 mmol) in dry DMSO (10 mL) under a nitrogen atmosphere. Heat the mixture to 80C for four hours. Cool the reaction to room temperature and pour into water (100 mL). Extract the aqueous phase with Et20 (2 x 50 mL) and wash the combined organic layers with water (50 mL). Dry over sodium sulfate and concentrate in vacuo. Chromatograph the residue on a Si02 column eluting the material with EtOAc in hexanes (10 to 40%) to give 200 mg of the title compound (34%).

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; ELI LILLY AND COMPANY; WO2004/9086; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 630-17-1, 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. 630-17-1 name is 1-Bromo-2,2-dimethylpropane, 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.

5-Bromo-2-hydroxy-1-cyanobenzene (1.0 g, 5.0 mmol) was dissolved in DMF (10 mL), add K2CO3 (2.1 g, 15.0 mmol), stir at room temperature for 1.0 h, add bromo neopentane (2.3 g, 15.0 mmol), and react at 80 C for 3 h.TLC followed the reaction completely. It was cooled to room temperature, diluted with 100 mL of water, and extracted with ethyl acetate (100 mL¡Á3), purified by silica gel column chromatography (ethyl acetate V: V petroleum ether = 1: 20) to give 5-bromo-2-neopentyloxybenzonitrile (a5)1.22 g, yield 90%

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-2,2-dimethylpropane, and friends who are interested can also refer to it.

Reference:
Patent; South China University of Technology; Li Jing; Li Xiaolei; Li Yuanyuan; Zhou Haiyan; Zhang Lei; Guan Su; (21 pag.)CN110078668; (2019); A;,
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. 615-55-4, name is 3,4-Dibromoaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: 3,4-Dibromoaniline

A mixture of 6.20g (26.6mmol)of 4-chloro-6-nitro-quinoline-3-carbonitrile and 8.00g (31.9mmo1) of 3,4-dibromoaniline in 160mL of ethanol was refluxed under N2 for 5h. Saturated sodium bicarbonate was added and volatile material was removed. The residue was slurried with hexane, collected, washed with hexane and water and dried. The insoluble material was repeatedly extracted with boiling ethyl acetate and the solution was then filtered through silica gel. The solvent was removed to give 3.80g of green solid: mass spectrum (electrospray, m/e): M+H 449.

The synthetic route of 615-55-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wyeth Holdings Corporation; EP1950201; (2008); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 55289-36-6, A common heterocyclic compound, 55289-36-6, name is 3-Bromo-2-methylaniline, molecular formula is C7H8BrN, 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.

Intermediate 1A: 2-Amino-N-(3-bromo-2-methylphenyl)-3-fluorobenzamide Method 1: A solution of 8-fluoro-1H-benzo[d][1,3]oxazine-2,4-dione (2.00 g, 11.04 mmol) and 3-bromo-2-methylaniline (4.11 g, 22.08 mmol) in dioxane (20 mL) in sealed reaction vessels was heated at 110 C. for 4 days. The cooled mixture was treated with 10% aqueous K2CO3 and stirred at room temperature for 30 min. The mixture was extracted with DCM 3 times, and the combined organic phases were washed with water, dried and concentrated. The residue was triturated with ether to give a gray solid (2.50 g). The mother liquor was concentrated and the residue was again triturated with ether to give a gray solid (230 mg). The two solids were combined to provide 2-amino-N-(3-bromo-2-methylphenyl)-3-fluorobenzamide as a gray solid (2.73 g, 78% yield). Mass spectrum m/z 323, 325 (M+H)+.; Method 2. A suspension of 8-fluoro-1H-benzo[d][1,3]oxazine-2,4-dione (3.00 g, 16.6 mmol) in xylenes (50 mL) was treated with 3-bromo-2-methylaniline (3.08 g, 16.6 mmol) and heated to reflux. After 6 h the mixture was allowed to cool to room temperature overnight. The resulting suspension was diluted with hexanes and the precipitate was collected by filtration, rinsed with hexanes and air-dried to provide 2-amino-N-(3-bromo-2-methylphenyl)-3-fluorobenzamide as a white solid (4.50 g, 84% yield). 1H NMR (400 MHz, chloroform-d) delta 7.69 (d, J=7.9 Hz, 1H), 7.65 (br. s., 1H), 7.50-7.46 (m, 1H), 7.32 (d, J=8.1 Hz, 1H), 7.19-7.11 (m, 2H), 6.73-6.64 (m, 1H), 5.69 (br. s., 2H), 2.44 (s, 3H).

The synthetic route of 55289-36-6 has been constantly updated, and we look forward to future research findings.

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

Application of 33070-32-5, These common heterocyclic compound, 33070-32-5, name is 5-Bromo-2,2-difluorobenzodioxole, 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.

Step 1: A mixture of 5-bromo-2,2-difluoro-1,3-benzodioxole (15.0 g, 63.6 mmol), ethyl cyanoacetate (14.4 g, 127 mmol) and Na3PO4 (31.2 g, 191 mmol) in toluene (180 mL) was degassed three times and back filled with N2. Then Pd(dba)2 (1.46 g, 2.54 mmol) and PtBu3 (10% w/w in hexane, 10.3 g, 5.08 mmol) were added. H20 (0.9 mL) was added and the mixture was degassed three times and back filled with N2. The mixture was heated at 90C for 18 hours. The mixture was diluted with EtOAc (200 mL) and filtered. The filtrate was washed with H20 (100 mL) and brine (50 mL), dried over Na2SO4, filtered and concentrated to give 17 g of crude ethyl 2-cyano-2-(2,2-difluorobenzo[d][1,3]dioxol-5- yl)acetate as a black oil, which was used directly for the next step.

Statistics shows that 5-Bromo-2,2-difluorobenzodioxole is playing an increasingly important role. we look forward to future research findings about 33070-32-5.

Reference:
Patent; N30 PHARMACEUTICALS, INC.; SUN, Xicheng; QIU, Jian; STOUT, Adam; WO2014/186704; (2014); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 10485-09-3, name is 2-Bromoindene, 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 10485-09-3, category: bromides-buliding-blocks

(Production example 1) Synthesis of (dimethylsilylene) 2 (indene) 2 Under nitrogen flow, a 1L three-necked flask receives 50 mL of THF and 2.5 g (41 mmol) of Mg. To this 0.1 mL of 1,2-dibromoethane is added and the mixture is stirred to activate Mg. After stirring for 30 minutes, the solvent is removed and 50 mL of THF is newly added. To this, a solution of 5.0 g (25.6 mmol) of 2-bromoindene in THF (200 mL) is added dropwise over 2 hours. After completion of the addition followed by stirring at room temperature for 2 hours followed by cooling to -78C, a solution of 3.1 mL (25.6 mmol) of dichlorodimethylsilane in THF (100 mL) is added dropwise over 1 hour. After stirring for 15 hours, the solvent is evaporated off. The residue was extracted with 200 mL of hexane and the solvent was distilled off to obtain 6.6 g (24.2 mmol) of 2-chloromethylsilylindene (yield: 94%).

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; IDEMITSU PETROCHEMICAL CO. Ltd.; EP1095951; (2001); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 3344-70-5, These common heterocyclic compound, 3344-70-5, name is 1,12-Dibromododecane, 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: All compounds were prepared according to previously described procedures [16,17]. Briefly, a phenol derivative (0.015 mol) and a dibromoalkane (0.0075 mol) were dissolved in a mixture of ethanol and water (9/1) containing an alkaline hydroxide (0.015 mol). The mixture was heated under microwave irradiation in an Initiator? Biotage oven for 20 min at 120 ¡ãC. After cooling, the precipitate was filtered and thoroughly washed with water, ethanol and ether.

The synthetic route of 3344-70-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Cappoen, Davie; Forge, Delphine; Vercammen, Frank; Mathys, Vanessa; Kiass, Mehdi; Roupie, Virginie; Anthonissen, Roel; Verschaeve, Luc; Vanden Eynde, Jean Jacques; Huygen, Kris; European Journal of Medicinal Chemistry; vol. 63; (2013); p. 731 – 738;,
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. 100189-84-2, name is 2,5-Dibromo-1,3-dimethylbenzene, This compound has unique chemical properties. The synthetic route is as follows., name: 2,5-Dibromo-1,3-dimethylbenzene

Step 2: synthesis of (E)-3-(4-bromo-3,5-dimethylphenyl)acrylonitrile (compound lb) Compound lb [0250] To a solution of 2,5-dibromo-l ,3-dimethylbenzene (2640 mg, 10 mmol, Oakwood Products, Inc. – 018507) in anhydrous acetonitrile (25 mL) was added palladium(II) acetate (1 12 mg, 0.5 mmol), acrylonitrile (531 mg, 10 mmol), tri(o-tolyl)phosphine (131 mg, 0.5 mmol) and triethylamine (4 mL, 30 mmol) then the mixture was purged with argon and heated at 1 10 C for 2 hours. The reaction mixture was filtered through Celite and the filter pad was washed with tetrahydrofuran (10 mL). The filtrate was evaporated then re-dissolved with ethyl acetate (50 mL). The solution was washed with water (50 mL). The water layer was back extracted with ethyl acetate (50 mL). The combined organics were washed with brine (30 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure to give a crude residue. This was subjected to silica gel chromatography (gradient from 0-20% ethyl acetate in wo-hexanes) to afford the crude product which was treated in sonic bath with hexane (10 mL) for 10 minutes. The product precipitated out of solution and was collected by filtration. The solids were washed with cold hexane to afford compound lb. NMR (400 MHz, CDC13) 6 7.25 (d, J= 16.6 Hz, 1H), 7.12 (s, 2H), 5.84 (d, J = 16.6 Hz, 1H), 2.42 (s, 6H). LCMS (m/z) no MS signal, Tr = 2.78 min (LCMS method 2).

According to the analysis of related databases, 100189-84-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GILEAD SCIENCES, INC.; INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY OF THE AS CR, V.V.I.; JANSA, Petr; SIMON, Tetr; LANSDON, Eric; HU, Yunfeng, Eric; BASZCZYNSKI, Ondrejj; DEJMEK, Milan; MACKMAN, Richard, L.; (185 pag.)WO2016/105564; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 33786-90-2,Some common heterocyclic compound, 33786-90-2, name is 5-Bromobenzene-1,3-diamine, molecular formula is C6H7BrN2, 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.

A round bottom flask was charged 5-bromo-1 ,3-diaminobenzene (3.7 g, 19.8 mmol) and suspended in water (20 ml_). Di-ferf-butyl dicarbonate (9.50 g, 43.56 mmol) was added causing heating and effervescence. The reaction mixture was further diluted with water (80 ml_) then heated at 70 ¡ãC for 5 h. On cooling to room temperature, water (100 ml_) was added, the precipitate collected by filtration and thoroughly washed with water. The solid residue was extracted into dichloromethane (100 ml_), dried over magnesium sulphate, filtered and concentrated to dryness to give the title compound as a pale yellow solid (7.4 g, 96percent). LCMS [M+Na]+ = 411.0.

The synthetic route of 33786-90-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VECTUS BIOSYSTEMS LIMITED; DUGGAN, Karen Annette; (120 pag.)WO2018/18091; (2018); 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. 1073-39-8, name is 3-Bromobicyclo[4.2.0]octa-1,3,5-triene, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H7Br

To a solution of 3-bromobicyclo[4.2.0]octa-1,3,5-triene (132 mg, 0.72 mmol) in THF (1.5 ml) was added dropwise n-BuLi (2.5 M in n-hexane) (0.29 ml, 0.72 mmol) at -78C under N2. The reaction mixture was stirred at -78C for 30 min. 4-(Benzyloxy)-3-bromo-5-methylbenzaldehyde (200 mg, 0.66 mmol) in THF (0.5 ml) was added dropwise at -78C. The reaction mixture was stirred at -78 C for 1 h. Saturated NH4CI (aq) was added and the mixture was extracted with EA thrice. The combined extracts were washed with water, saturated brine and dried over anhydrous Na2S04, then concentrated and purified by chromatography on silica gel (1 :3 EA/PE) to yield (4-(benzyloxy)-3- bromo-5-methylphenyl)(1,2-dihydrocyclobutabenzen-4-yl)methanol as a yellow oil.

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