Tag: M.W=200-300

Synthetic Route of 33070-32-5, A common heterocyclic compound, 33070-32-5, name is 5-Bromo-2,2-difluorobenzodioxole, molecular formula is C7H3BrF2O2, 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 cold solution of 5-bromo-2,2-difluorobenzo[(f] [l ,3]dioxole (5.75 mL, 42.2 mmol) in tetrahydrofuran (80 mL) was added a 2.0 M solution of isopropylmagnesium chloride in tetrahydrofuran (28.1 mL, 56.1 mmol) within 5- 10 minutes while maintaining the temperature in the range of 10-20 C. The reaction mixture was stirred at the same temperature for another 15 minutes and then allowed to attain room temperature with continued overnight stirring. The reaction mixture was cooled with an ice bath, triisopropyl borate (12.74 mL, 54.9 mmol) was added dropwise over 2 minutes, and stirring at room temperature was continued for 30 minutes. The reaction mixture was cooled to 10 C and 10% H2SO4 solution (50 mL) was added slowly which resulted in a slight exotherm to 20 C. After stirring for 15 minutes, the mixture was partitioned between water and ethyl acetate, and the combined organic extracts were washed with saturated NaHCC>3 solution. The organic layer was separated, dried over magnesium sulfate, filtered, and concentrated. The residue was dissolved in 100 mL of teri-butyl methyl ether and cooled to 0 C. 30% Hydrogen peroxide solution in water (5.39 mL, 52.7 mmol) was added slowly, followed by water (60 mL), and the mixture was stirred overnight while warming up to ambient temperature. The reaction mixture was diluted with ethyl acetate and washed twice with sodium thiosulfate solution and brine. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated, and the residue was purified on silica gel(0-50% ethyl acetate in heptane) to give 6.43 g of the title compound as an amber oil.JH NMR (400 MHz, DMSO- ) delta ppm 9.75 (s, 1H), 7.12 (d, / = 8.7 Hz, 1H), 6.75 (d, / = 2.4 Hz, 1H), 6.52 (dd, / = 8.7, 2.5 Hz, 1H). MS (ESI-) mJz 173.1 (M-H)

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; CALICO LIFE SCIENCES LLC; ABBVIE INC.; MARTIN, Kathleen, Ann; SIDRAUSKI, Carmela; PLIUSHCHEV, Marina, A.; FROST, Jennifer, M.; TONG, Yunsong; BLACK, Lawrence, A.; XU, Xiangdong; SHI, Lei; ZHANG, Qingwei, I.; CHUNG, Seungwon; XIONG, Zhaoming; SWEIS, Ramzi, Farah; DART, Michael, J.; BROWN, Brian, S.; MURAUSKI, Kathleen; (673 pag.)WO2019/90069; (2019); A1;,
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Related Products of 129316-09-2,Some common heterocyclic compound, 129316-09-2, name is 1,3-Dibromo-5-(tert-butyl)benzene, molecular formula is C10H12Br2, 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.

Preparative Example P23Step 1 : 2-(3-Bromo-5-(tert-butyl)phenyl)propan-2-ol (P23a) To a solution of 1 ,3-dibromo-5-ferr-butylbenzene (404 mg) in dry THF (10 mL) was added n- BuLi (0.84 mL) at -78C and after 20 min, acetone was added dropwise to the above solution at -78C and the mixture was stirred at this temperature for 30 min and at rt for 1 h, diluted with sat. NH4CI and extracted with EA (3 x 30 mL). The organic layer was dried over Na2S04, evaporated and purified by CC to give compound P23a (380 mg, 70%) as a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,3-Dibromo-5-(tert-butyl)benzene, its application will become more common.

Reference:
Patent; PHENEX PHARMACEUTICALS AG; STEENECK, Christoph; KINZEL, Olaf; GEGE, Christian; KLEYMANN, Gerald; HOFFMANN, Thomas; WO2012/139775; (2012); A1;,
Bromide – Wikipedia,
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Related Products of 13633-25-5, 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. 13633-25-5 name is 1-Bromo-4-phenylbutane, 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.

Step 1. In a 250 ml three-necked flask, 1 g of a catalyst P-W2CNC, 1-bromo-4-phenylbutane 8.0 g, DMF 50 ml, and mechanical stirring were sequentially added.Put 1.8 g of methylparaben, K2CO 33.6 g, and heat to 115 C.Reaction 11h;Step 2: After the reaction is cooled to room temperature, the K2CO3 solid is removed by suction filtration.Add 50 ml of water to the filtrate, turbid, stir for 10 min, add about 3 mol / L of HCl solution to adjust pH = 2;Step 3. Extract the above system with dichloromethane, wash with ionized water,The solvent dichloromethane was removed by rotary evaporation to give an orange liquid;Step 4, the orange liquid is placed in a single-mouth bottle, 3.0 g of NaOH, 50 ml of water and 40 ml of ethanol are added, and the mixture is refluxed for 3 hours in an oil bath, and the ethanol is distilled off.The residue was adjusted to pH=2 with 3 mol/L of HCl;Step 5, after extracting the above system with dichloromethane, the organic phase is steamed.A sticky yellow solid was obtained, and after adding an appropriate amount of isopropanol, the mixture was stirred, solid crystallized, and suction filtered to give white crystals of 4-(4-phenylbutoxy)benzoic acid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-4-phenylbutane, and friends who are interested can also refer to it.

Reference:
Patent; Yang Cheng Feiyang; Yang Chengfeiyang; Chen Huaqi; (7 pag.)CN108689843; (2018); A;,
Bromide – Wikipedia,
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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. 67344-77-8, name is 1-(3-Bromophenyl)-N-methylmethanamine, A new synthetic method of this compound is introduced below., category: bromides-buliding-blocks

Step 1 : N-(3-Bromobenzyl)-N-methylacetamideTo a DMF (0.1 M) solution of 3-bromo-N-methylbenzylamine (1 eq.), Hunig’s base (3 eq) and 4-(dimethylamino)pyridine (5percent loading) was added acetyl chloride (1.5 eq). The resulting reaction mixture was stirred at RT for 16 h. After quenching the reaction with sat. aq. NaHCO3, the mixture was extracted with EtOAc. The organic extract was washed with 10percent aq. HCl, sat. aq. NaHCO3, and brine. Drying over Na2SO4, filtration and concentration of the filtrate in vacuo afforded the crude product as a yellow oil. Purification by way of flash chromatography (SiO2, 4: 1 (v/v) Hex : EtOAc -> EtOAc) afforded the title compound as a yellow oil.

The synthetic route of 67344-77-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK FROSST CANADA LTD.; WO2007/9250; (2007); A1;,
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Application of 57946-63-1, 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 57946-63-1 as follows.

Commercially available 2-bromo-4-(trifluoromethyl)benzeneamine (2.06 g, 8.6 mmol) was suspended in concentrated HCl (4.0 mL). Clumps of material were broken up with a spatula, then ice (-2.6 g) was added to the mixture and it was cooled over an ice bath. A solution of NaNO2 (0.64 g, 9.3 mmol) in H2O (2.6 mL) was added dropwise while maintaining the temperature of the reaction mixture at 0-50C. The mixture was stirred for 20 minutes over the ice bath, then poured slowly into a solution of KI (12.5 g, 75.3 mmol) in H2O (16 mL). The BCI mixture was stirred for several minutes, then left to settle over night. EPO The reaction mixture was extracted thrice with hexanes. The combined organics were washed twice with IM NaOH, once with aqueous sodium bisulfite solution, then with brine. The solution was dried over MgSO4, vacuum filtered through Celite.(R). and cone in vacuo to give 2.33 g of 2-bromo-4-(trifluoromethyl)-iodobenzene. By TLC (100percent hexanes) and 1H NMR analysis, it was determined that the product was of sufficient purity to be used in the subsequent step. The resultant diethyl [2-bromo-4-(trifluoromethyl)- phenyljdifluoromethylphosphonate was synthesized from 2-bromo-4-(trifluoromethyl)- iodobenzene according to Example 25 except that chlorotrimethylsilane (several drops) was used in place of acetic acid. Compound 86 was synthesized according to procedures similar to those of Example 40 from this corresponding diethyl phosphonate. MS (ES-):m/z 352.9, 354.9 (M – H). 1H NMR: (DMSO-d6, 400 MHz) delta 8.07 (s, IH), 7.89 (d, J = 8.0, IH), 7.78 (d, J = 8.0, IH).

According to the analysis of related databases, 57946-63-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CEPTYR, INC.; WO2006/55525; (2006); A2;,
Bromide – Wikipedia,
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Related Products of 327-52-6, 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. 327-52-6, name is 1-Bromo-2,4,5-trifluorobenzene, This compound has unique chemical properties. The synthetic route is as follows.

Example 1 Preparation of (3S)-methyl 3-(tert-butoxycarbonylamino)-4-hydroxy-4-(2,4,5-trifluorophenyl)butyrate 13.2 g metal magnesium and 400 ml tetrahydrofuran were added into a clean flask. 116.05 g trifluorobromobenzene was added thereto dropwisely after initiation by iodine and the reaction was kept at 30-40 C. for 3 hours for use. 29.9 g (S)-methyl 3-(tert-butoxycarbonyl amino)-4-oxo-n-butyrate was dissolved in 300 ml THF, and cooled to -20 C. The solution mentioned above was added thereto dropwisely over two hours and kept at the temperature for 3 hours. 400 ml ammonium chloride solution was added dropwisely. Layers were separated. The aqueous layer was extracted with tetrahydrofuran. The organic layer was dried and concentrated to get 14.5 g (3S)-methyl 3-(tert-butoxy carbonylamino)-4-hydroxy-4-(2,4,5-trifluoromethyl-phenyl)butyrate (yield: 66%).

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-2,4,5-trifluorobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Zhu, Guoliang; Zhang, Jian; Yang, Lljun; Yao, Qingdan; Ying, Jie; US2012/178957; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 69038-76-2, name is 4-Bromo-N1-methylbenzene-1,2-diamine, 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 69038-76-2, Quality Control of 4-Bromo-N1-methylbenzene-1,2-diamine

A mixture of 4-bromo-N1-methylbenzene-1,2-diamine (19) (250 mg, 1.2434 mmol, 1 equiv) and bisulfite adduct of benzaldehyde (392 mg, 1.8651 mmol, 1.5 equiv) in 4 mL DMF was stirred at 60?C for 4h. The reaction mixture was diluted with water and extracted with EA. The organic layer was dried, filtered and evaporated. The crude 20a (236.8 mg, 66.3% yield) was used in the next step without purification. Mp 147.6-149.9 C (150-152 C [13]). HRMS m/z calculated for C14H11N2Br [M+H]+ 287.0184, found: 287.0190. CAS No. 760212-73-5

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, 4-Bromo-N1-methylbenzene-1,2-diamine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Cal??kan, Burcu; Banoglu, Erden; Guer Maz, Tu?ce; Nocentini, Alessio; Supuran, Claudiu T.; Uslu, Azize Gizem; Bioorganic Chemistry; vol. 95; (2020);,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 327-51-5, A common heterocyclic compound, 327-51-5, name is 1,4-Dibromo-2,5-difluorobenzene, molecular formula is C6H2Br2F2, 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.

100 g of intermediate 2-1, 186 g of intermediate 1-2, 203 g of potassium carbonate, 23.7 g of tetrabutylammonium bromide (TBAB) were added to a 2 L three-necked flask, and 800 ml of toluene, 200 ml of ethanol, and 200 ml of water were successively added. Nitrogen gas was added, stirred for 15 min, 2.1 g of tetrakis(triphenylphosphine)palladium was added, and the mixture was heated to 80 C for refluxing for 8 hours. The TLC was used to monitor the reaction of the starting materials and then cooled to room temperature.The impurities were separated, and the organic phase was washed with water until neutral. After drying over anhydrous sodium sulfate, the residue was purified by silica gel column to obtain 107.9 g of intermediate 2 in a yield of 92.2%.

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; Xi’an Ruilian New Materials Co., Ltd.; Sun Jun; Zhang Hongke; Liu Kaipeng; Yang Dandan; Tian Mi; He Haixiao; Li Jiangnan; Wang Xiaowei; Liu Qianfeng; Gao Renxiao; (33 pag.)CN109535131; (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. 944718-31-4, name is 5-Bromo-1-methyl-1H-benzo[d][1,2,3]triazole belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 5-Bromo-1-methyl-1H-benzo[d][1,2,3]triazole

A mixture of 5-bromo-l-methyl-liT-benzo[7][l,2,3]triazole (302.3 mg, 1.426 mmol), diphenylmethanimine (342.5 mg, 1.890 mmol), t-BuONa (274.2 mg, 2.853 mmol), BINAP (87.8 mg, 0.141 mmol) and Pd2(dba)3 (131.4 mg, 0.1435 mmol) in l,4-dioxane (10 mL) was heated to 100 °C and stirred for 6 hours under N2 atmosphere and concentrated in vacuo. The residue was diluted with water (50 mL) and the resulting mixture was extracted with a mixed solvent of DCM/MeOH (10/1 (v/v), 80 mLx 3). The combined organic layers were dried over anhydrous Na2S04 and concentrated in vacuo to give the title compound as a brown solid (445.4 mg), which was used directly in the next step without further purification. MS (ESI, pos.ion) m/z: 313.2 [M+H]+.

The synthetic route of 944718-31-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; CALITOR SCIENCES, LLC; XI, Ning; LI, Minxiong; PENG, Ju; LI, Xiaobo; ZHANG, Tao; HU, Haiyang; CHEN, Wuhong; BAI, Changlin; KE, Donghua; CHEN, Peng; (281 pag.)WO2019/99311; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 626-40-4, 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. 626-40-4, name is 3,5-Dibromoaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Compound II (2.25 g, 10 mmol),Compound III (2.51 g, 10 mmol)And diisopropylethylamine(DIPEA,3.88 g, 30 mmol)Dissolved in 50 mL of dry xylene,And then heat up under nitrogen protectionReflux,Until the reaction is complete (usually 5 hours).The reaction mixture was carefully poured into 200 mL of ice water, stirred, extracted with 50 mL of X3CH2C12,Combined extraction phase,Washed sequentially with 1% dilute hydrochloric acid (200 mL) and brine (100 mL)Dried over anhydrous sodium sulfate. The desiccant was removed by suction filtration,The filtrate was evaporated to dryness on a rotary evaporator,Compound IV was obtained as a white solid.

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, 3,5-Dibromoaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Guangdong Sai Bo Technology Co., Ltd.; Guo Huijun; (12 pag.)CN106831838; (2017); A;,
Bromide – Wikipedia,
bromide – Wiktionary