Tag: M.W=200-300

Reference of 608-30-0, 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. 608-30-0, name is 2,6-Dibromoaniline, This compound has unique chemical properties. The synthetic route is as follows.

Step 1: 1,3-dibromo-2-chlorobenzene To a mixture of isoamyl nitrite (585 mg, 5 mmol) and CuCl (396 mg, 4 mmol) in acetonitrile (10 mL) was slowly added 2,6-dibromoaniline (502 mg, 2 mmol) at 65 C. The reaction mixture was stirred at 65 C. for 2 h. and then NH4BF4 solution (4.2 g, 40 mmol) was added dropwise. The reaction mixture was stirred at 0-10 C. for 1 h, cooled to rt, concentrated under reduced pressure, dissolved with EA (30 mL), washed with water (20 mL). The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography eluted with PE to give 1,3-dibromo-2-chlorobenzene (270 mg, yield 49%) as solid.

The chemical industry reduces the impact on the environment during synthesis 2,6-Dibromoaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Anacor Pharmaceuticals, Inc.; Eli Lilly and Company; Akama, Tsutomu; Balko, Terry William; Defauw, Jean Marie; Plattner, Jacob J.; White, William Hunter; Winkle, Joseph Raymond; Zhang, Yong-Kang; Zhou, Yasheen; US2013/131016; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 1195-33-1, 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. 1195-33-1 name is 4-Bromobenzenesulfinic acid, 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.

General procedure: A sealable reaction tube equipped with a magnetic stirrer bar was charged with 2-(allyloxy)benzaldehyde (0.2mmol), benzenesulfinic acid (3.0 equiv.), Na2-Eosin Y (4 mol%), K2S2O8 (3.0 equiv.), DMF_H2O=1:1 (2 ml), 8W blue. The reaction vessel was carried out room temperature. After completion, it was diluted with ethylacetate, washed with water. After the solvent was removed under reduced pressure, the residue was purified bycolumn chromatography on silica gel to afford the corresponding product.

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

Reference:
Article; Chen, De-Mao; Han, Qing-Qing; Li, Guang-Hui; Sun, Yuan-Yuan; Wang, Zu-Li; Xu, Xin-Ming; Yu, Xian-Yong; Chinese Chemical Letters; (2020);,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 937046-98-5, name is 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine, 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. Computed Properties of C6H5BrN4

7-Bromopyrrolo[1,2-f][1,2,4]triazin-4-amine (2.264 mmol, 482 mg) and tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydropyridine-1(2H)carboxylate (2.264 mmol, 700 mg) were dissolved in dioxane (15 mL). 2 M-solution of potassium carbonate (5.66 mmol, 2.83 ml) in water was added. The resulting solution was purged with N2 5 minutes at 30 C. Tetrakis(triphenylphosphine)palladium(0) (0.113 mmol, 131 mg) was added and the resulting solution was purged another 5 minutes at 30 C with N2. The reaction was heated 6h at reflux. The reactionmixture was cooled to rt and water and EtOAc were added. The resulting suspension was filtered over decalite. The filtrate was extracted with EtOAc (2x). The combined organic layers were dried (Na2SO4), filtered and concentrated. The product was purified using silica gel chromatography (dichloromethane/methanol = 100/0 to 9/1 (v/v%) to give 250 mg of tert-Butyl 3-(4-aminopyrrolo[1,2-f][1,2,4]triazin-7-yl)-5,6-dihydropyridine-1(2H)-carboxylate (35%).

The synthetic route of 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MSD Oss B.V.; Man, de, Adrianus, Petrus, Antonius; Sterrenburg, Jan-Gerard; Raaijmakers, Hans C.A.; Kaptein, Allard; Oubrie, Arthur A.; Rewinkel, Johannes, Bernardus, Maria; Jans, Christiaan, Gerardus, Johannes, Maria; Wijkmans, Jacobus C.H.M.; Barf, Tjeerd A.; Gao, Xiaolei; Boga, Sobhana Babu; Yao, Xin; Zhu, Hugh Y.; Cooper, Allen B.; Kim, Ronald M.; EP2548877; (2013); A1;,
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 2862-39-7 as follows. name: 2-Bromo-N,N-dimethylethanamine hydrobromide

A mixture of tert- butyl 5-{N-[(4-methoxyphenyl)methyl]3-fluoro-4-[2-(1H-imidazol-1-yl)acetamido]benzenesulfonamido}-1,3-thiazole-4-carboxylate (Example 20a) (250 mg, 0.4 mmol), dimethylaminoethyl bromide hydrobromide salt (Sigma Aldrich) (120 mg, 2.07 mmol) and DIPEA (0.61 mL, 3.3 mmol) in acetonitrile (30 mL) was heated at 80 C for 72 hours. The mixture was evaporated and the residue triturated with methanol-ether affording a brown solid (300 mg).

According to the analysis of related databases, 2862-39-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Antabio SAS; DAVIES, David; LEIRIS, Simon; (56 pag.)EP3572411; (2019); 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. 2635-13-4, name is 5-Bromobenzo[d][1,3]dioxole, A new synthetic method of this compound is introduced below., SDS of cas: 2635-13-4

Step 1g. 5-Bromo-6-iodobenzo[d][1,3]dioxole (Compound 0107-1) A solution of compound 0106 (10.0 g, 50.0 mmol), anhydrous acetonitrile (150 mL), TFA (11.4 g, 100.0 mmol) and NIS (33.7 g, 150.0 mmol) was stirred at room temperature for 24 h. The solvent was removed under reduce pressure and the crude purified by column chromatography on silica gel (petroleum) to yield the title compound 0107-1 as a white solid (18.5 g, 91%): 1H NMR (DMSO-d6) delta 5.99 (s, 2H), 7.10 (s, 1H), 7.26 (s, 1H).

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; Cai, Xiong; Qian, Changgeng; Zhai, Haixiao; US2008/234314; (2008); 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. 28342-75-8, name is 1,5-Dibromo-2,4-difluorobenzene, A new synthetic method of this compound is introduced below., COA of Formula: C6H2Br2F2

Under a nitrogen atmosphere, 1,5-dibromo-2,4-difluorobenzene (600.0 g),carbazole (81.1 g), potassium carbonate (91.0 g of) and NMP (300ml) was heated to 155 and It was stirred for 4 hours. The reaction mixture was cooled until room temperature,water was added to make the inorganic salt is dissolved, and the organics were extractedby suction filtration. After washing with ethyl acetate, dissolved in heated odichlorobenzene,and the short silica gel column (eluent: o-dichlorobenzene) by. Afterthe solvent was distilled off under reduced pressure, and then washed with ethylacetate, to obtain 9,9 ‘- (4,6-dibromo-1,3-phenylene) bis (9H-carbazole) (108.0 g of) .

The synthetic route of 28342-75-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kwansei Gakuin School Corporation; Tian, Shanzuoci; Zhong, Zhongzongyiliang; Zhong, Daoguiyi; Ping, Jingdagui; Xiao, Yeyangping; Zhi, Lianyizhi; Ni, Jingping; Song, Xiawusi; Sheng, Tianlizhao; (405 pag.)CN105431439; (2016); A;,
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. 54962-75-3, name is 3-Bromo-5-(trifluoromethyl)aniline, A new synthetic method of this compound is introduced below., name: 3-Bromo-5-(trifluoromethyl)aniline

Example 1: Preparation of 3-(trifluoromethyl)-5-(4-methyl-1H-imidazole-1-yl)-benzeneamine of formula I 2000g of 3-bromo-5- trifluoromethylaniline of formula II, 1368g of 4-methylimidazole of formula III , 181 g of 8-hydroxyquinoline, 238g of CuI, 666.6g of NaOH, 933g of CaO and 7000ml of DMSO were loaded into a lOL of 3-neck flask. The reaction mixture was protected with nitrogen and was then stirred at 120C for 69 hours while monitoring for the consumption of 3-bromo-5- trifluoromethyaniline by HPLC. Heating was stopped when 3-bromo-5- trifluoromethyaniline / 4-methylimidazole is not more than 5%. The reaction mixture was cooled down to 45-50C and poured into a 50L reactor. 8.4L of 14% ammonia was added dropwise and then stirred for 1hour at 45-50C. The mixture was cooled down to room temperature.16.8L of water and 10L of ethyl acetate were added to the extract. The upper organic layer was separated and filtered through the filter aid. The lower aqueous layer was washed with 7.5L of ethyl acetate and combined with the above filtrate. The combined organic layer was washed with 5Lx3 of 5% of brine for three times. The upper organic layer was separated and dried over 1kg of anhydrous Na2S04 overnight. The mixture was filtered and concentrated to obtain 2.3kg of solid. The residue was dissolved in 2L of ethyl acetate at 45C. To the solution was then added 8L of petroleum ether dropwise at 45C. The mixture was cooled down slowly to 0-15C and stirred for 1hour. A large amount of precipitate was formed and filtered. The filtered cake was dissolved in 2L of ethyl acetate at 45C. The solution was then added 8L of petroleum ether dropwise at 45C. The mixture was cooled down slowly to 15-0C and stirred for 1hour. A large precipitate was formed and filtered. The filter cake was dried at 45C and 954g of 3-(trifluoromethyl)-5-(4-methyl-1H-imidazole-l-yl)-benzeneamine of formula I were obtained. (Yield: 47.5%). The obtained compound of formula I had purity of 99.7% on area by HPLC and contained 0.13% on area by HPLC, of the 5 methyl isomer impurity.

The synthetic route of 54962-75-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Teva Pharmaceutical Industries Ltd.; EP2305667; (2011); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

22034-13-5, name is 4-Bromobenzo[c][1,2,5]thiadiazole, 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. Product Details of 22034-13-5

A 100 mL round bottom flask is charged with 4-bromobenzo[cl[1,2,Slthiadiazole (1.61 g, 7.49 mmol, 1.00 equiv), tert-butyl (4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)carbamate (2.74 g, 8.24 mmol, 1.10 equiv), potassium carbonate (3.10 g, 22.5 mmol, 3.00 equiv), and [1,1? -Bis(diphenylphosphino)ferrocenel dichloropalladium(ll) (0.274 g, 0.374 mmol, 5.00 molpercent). The flask is connected to a reflux condenser and is placed under a nitrogen atmosphere. 38 mL of nitrogen-sparged 9:1 dioxane:water is added and the mixture was stirred at 100°C overnight.The solution is cooled and quenched with water. Product is extracted with several portions of dichloromethane. Combined organic fractions are dried with Mg504, concentrated, and purified by chromatography on silica gel (20percent EtOAc in hexane). A white solid is isolated. The material is immediately dissolved in 30 mL dichloromethane and 3 mL concentrated HC1 are added. The mixture is stirred at ambient temperature overnight. The slurry is filtered, and the isolated white solid is rinsed with a few additional portions of dichloromethane. The solid is dried in a vacuum oven for several hours. Proton/CarbonNMR are consistent with the HC1-salt of the desired product. ?H NMR (500 MHz, DMSOd 6) oe 8.62 (s, 3H), 8.11 (dd, J= 8.7, 1.1 Hz, 1H), 8.06?7.96 (m, 2H), 7.88 (dd, J=7.0, 1.1 Hz, 1H), 7.82 (dd, J= 8.6, 7.0 Hz, 1H), 7.68 (d, J= 8.1 Hz, 2H), 4.11 (s, 2H). ?3C NMR (126 MHz, DMSO-d6) oe 154.95, 152.61, 136.77, 134.14, 132.71, 130.08, 129.16, 129.07, 128.01, 120.61, 41.81.

The synthetic route of 22034-13-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DOW GLOBAL TECHNOLOGIES LLC; YOUNG, Kaylie L.; CUMMINS, Clark H.; GLOVER, William C.; GRIGG, Robert David; (26 pag.)WO2019/27608; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 58971-11-2, 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 58971-11-2 as follows.

General procedure: To compound 5, 6 or 7 (1 equiv) and the appropriate alkylamine(1.3 equiv) in anhydrous DMF (10 mL/mmol) were added DIEA (3equiv) and PyBOP (1 equiv), and the reaction mixturewas stirred atroom temperature under argon. When the reaction was complete(2 h – 4 h), the solvents were removed under reduced pressure togive a residue that was taken up in CH2Cl2. The solution waswashed with saturated aqueous NaHCO3, then water. The organiclayer was dried over Na2SO4 and then evaporated in vacuo. Purificationby flash chromatography afforded the corresponding amidederivatives 8, 9 or 10 (yield: 40-76%).

According to the analysis of related databases, 58971-11-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Paoletti, Julie; Assairi, Liliane; Gelin, Muriel; Huteau, Valerie; Nahori, Marie-Anne; Dussurget, Olivier; Labesse, Gilles; Pochet, Sylvie; European Journal of Medicinal Chemistry; vol. 124; (2016); p. 1041 – 1056;,
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. 327-51-5, name is 1,4-Dibromo-2,5-difluorobenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 327-51-5

under a nitrogen atmosphere, to a 500ml reaction vessel 2,3-dibromo-thiophene (Wako Pure Chemical Industries, Ltd.) added to 15g and THF160ml did. This solution under ice-cooling ethyl magnesium chloride (Sigma-Aldrich, 2.0M) was added to THF solution 32ml (63mmol) of, and stirred for 10 minutes at the same temperature, 3-bromothiophene-2-magnesium chloride (3-halo thiophene-2-magnesium halide) was prepared. It added another 1l reaction vessel to zinc chloride (Wako Pure Chemical Industries, Ltd.) 10g (73mmol) and THF100ml, was a fine white slurry was stirred under ice-cooling. Then 3-bromo-2-magnesium chloride in an ice-cold solution of the (water bath temperature 10 C) was transferred to the zinc chloride solution, and the mixture was stirred for 30 minutes. Further the temperature was raised to room temperature, stirred for 10 minutes, 3-bromo-2-zinc chloride (3-halo-2-zinc derivative) was prepared. To this mixture 1,4-dibromo-2,5-difluorobenzene (Wako Pure Chemical) 5.5 g (20 mmol), catalyst as tetrakis (triphenylphosphine) palladium (Tokyo Kasei Kogyo) 350 mg (0.30 mmol) (1 , it was added 1.5 mol%) on the 4-dibromo-2,5-difluorobenzene. After carrying out 25 hours cross-coupling reaction at 50 C, the reaction by the addition of water-cooled vessel 1N hydrochloric acid 90ml stopped. It was extracted with toluene and the organic phase was washed with brine, and dried with anhydrous sodium sulfate. Concentrated in vacuo, and filtered resulting residue in a small amount of silica gel, concentrated crystal was further washed with hexane. Heptane / toluene = purified by recrystallization from 2/1, to give a pale yellow solid 5.3g of 1,4-bis (3-bromo-2-thienyl) -2,5-difluoro-benzene (61% yield).

The synthetic route of 327-51-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tosoh Corporation; Ueda, Saori; Watanabe, Masato; (7 pag.)JP2016/74626; (2016); A;,
Bromide – Wikipedia,
bromide – Wiktionary