Tag: M.W=200-300

These common heterocyclic compound, 14862-52-3, name is 3,5-Dibromochlorobenzene, 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. name: 3,5-Dibromochlorobenzene

Compound 1 (30 g, 100 mmol) was dissolved in anhydrous i-Pr2O (300.0 mL) in a dried flask under nitrogen. The reaction mixture was cooled to -78 C and stirred under nitrogen atmosphere. A 2.5 M solution of n-BuLi in hexanes (40 mL, 100 mmol) was added dropwise to the above solution and the reaction mixture was stirred at -78 C for 30 min after complete addition of n-BuLi. N-methoxy-N-methylacetamide (12 g, 120.0 mmol) was added to the above reaction mixture, while keeping the reaction mixture below -78 C. After addition of N-methoxy-N-methylacetamide was completed, the reaction mixture was warmed slowly to room temperature for 30 min. The reaction mixture was poured into 40 mL of aqueous NH4Cl and the reaction mixture was stirred for 15 min. The organic phase was separated, dried over anhydrous MgSO4, filtered and evaporated in vacuo to give the compound 2 (25 g, crude) as a pale yellow viscous liquid.

The synthetic route of 3,5-Dibromochlorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SAINT LOUIS UNIVERSITY; RUMINSKI, Peter; GRIGGS, David; WO2014/15054; (2014); A1;,
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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. 468075-00-5, name is 2-Bromo-1-chloro-4-(trifluoromethoxy)benzene, This compound has unique chemical properties. The synthetic route is as follows., Formula: C7H3BrClF3O

General procedure: To a solution of Compound 6A (138 mg, 0.32 mmol) in tolunen (4 mL) was added N-methylpiperazine (160 mg, 1.6 mmol), t-BuONa (61 mg, 0.64 mmol), Pd2(dba)3 (29 mg, 0.032 mmol), and Xantphos (37 mg, 0.064 mmol) and heated in a microwave oven at 120 C for 2 hours. The mixture was concentrated and purified by reverse phase column chromatography to afford Compound 6B. LC-MS (ESI) m/z: 440 [M+H]+.

According to the analysis of related databases, 468075-00-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BIOMARIN PHARMACEUTICAL INC.; WANG, Bing; CHAO, Qi; (737 pag.)WO2019/133770; (2019); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 56961-77-4, name is 1-Bromo-2,3-dichlorobenzene, A new synthetic method of this compound is introduced below., Safety of 1-Bromo-2,3-dichlorobenzene

31.8 g (100.0 mmol) of Compound 11-A, 22.6 g (100.0 mmol) of Compound 1-B, 2.7 g (3.0 mmol) of Pd2(dba)3, 1.3 g (6.0 mmol) of PtBu3 (50% solution in toluene), 28.8 g (300.0 mmol) of NaOtBu were mixed with 1,500 mL of toluene under a nitrogen (N2) atmosphere, followed by stirring under reflux to allow a reaction to occur for 12 hours. At room temperature, an organic layer was separated therefrom using water and ethyl acetate, and the solvent was dried. Then, through silica gel column chromatography, 20.9 g of Compound 11-C was obtained at a yield of 45%. [0313] MS (MALDI-TOF) m/z: 463 [M]+

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; Samsung Display Co., Ltd.; KIM, Myeongsuk; YE, Jimyoung; YOO, Byeongwook; JEONG, Jaeho; (102 pag.)US2020/98991; (2020); A1;,
Chloride – Wikipedia,
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Synthetic Route of 38762-41-3, A common heterocyclic compound, 38762-41-3, name is 4-Bromo-2-chloroaniline, molecular formula is C6H5BrClN, 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 solution of 2,3,4-trifluorobenzoic acid (1 g, 5.68 mmol) and 4-bromo-2- chloroaniline (1.2 g, 5.68 mmol) in acetonitrile (10 mL) was added lithium amide (0.39 g, EPO 17.04 mmol) and the reaction stirred at 60 0C for 1.5 hours. The mixture was cooled to room temperature and then to 0 0C and acidified with aq. hydrochloric acid. The obtained precipitate was collected by filtration and washed with cold water and dried in vacuo to afford 2-[(4~bromo-2-chlorophenyl)amino]-3,4-difluorobenzoic acid (1.92 g, 94% yield) as a beige solid. MS (EI) for C13H7BrClF2NO2: 363 (MH+).

The synthetic route of 38762-41-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EXELIXIS, INC.; WO2007/44515; (2007); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 16793-91-2,Some common heterocyclic compound, 16793-91-2, name is 2-Chlorophenethyl Bromide, molecular formula is C8H8BrCl, 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.

Example 14: Preparation of 8-[2-(2-chlorophenyl)ethyl]-3-methyl-4-({4-[3-(trifluoromethyl)phenyl]piperazin-1-yl}carbonyl)-1-oxa-8-azaspiro[4.5]dec-3-en-2-one [Show Image] A mixture of 3-methyl-4-({4-[3-(trifluoromethyl)phenyl]piperazin-1-yl}carbonyl)-1-oxa-8-azaspiro[4.5]dec-3-en-2-one dihydrochloride (Example 1 , 200 mg, 0.40 mmol), anhydrous potassium carbonate (180 mg, 1.30 mmol) and 1-(2-bromo-ethyl)-2-chlorobenzene (0.07 mL, 0.22 mmol) in anhydrous N,N-dimethylformamide (3 mL) was heated at 90C for 1.5 hours under microwave irradiation. The reaction mixture was concentrated under vacuum. The residue was taken up in dichloromethane (20 mL), washed with water (20 mL) and brine (20 mL), dried (MgSO4) and concentrated under vacuum. After purification by flash chromatography (silica), the title compound was obtained as a white solid (76 mg, 34%). 1H NMR (DMSO-d6, 400 MHz): delta 7.46-7.34 (m, 3H), 7.26-7.23 (m, 4H), 7.11 (d, J = 7.5 Hz, 1 H), 3.80-3.79 (m, 1H), 3.68-3.69 (m, 1H), 3.56 (s, 2H), 3.27 (s, 1H), 3.16-3.15 (m, 2H), 2.93-2.92 (m, 1H), 2.87-2.83 (m, 4H), 2.53 (s, 2H), 2.25-2.24 (m, 3H), 1.88-1.87 (m, 1H), 1.76 (s, 3H), 1.72 (s, 1H), 1.52 (s, 1H). LCMS (Method D): Mass found (M+ 562), Rt (min): 4.64, Area (%): 99.5 (Max), 99.6 (254 nm). HPLC (Method A): Rt (min): 4.61, Area (%): 98.5 (Max), 99.3 (254 nm).

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

Reference:
Patent; Ares Trading SA; EP2508526; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 51572-93-1, 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. 51572-93-1 name is O-(2,4-Dichlorobenzyl)hydroxylamine hydrochloride, 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: To a solution of 3ae3e (1 mmol) in anhydrous ethanol (10 mL),corresponding O-benzylhydroxylamine hydrochloride (1 mmol)and NaOAc (1.2 mmol) were added and the resulting solution wasstirred at the room temperate for 3 h. The mixture was concentratedand taken in ethyl acetate (20 mL), washed with water(20 mL), saturated sodium chloride solution (20 mL) and dried oversodium sulfate. The resulting solution was concentrated and thepurification of the residue by recrystallization from ethanol yieldedthe desired compounds 4a-4t

At the same time, in my other blogs, there are other synthetic methods of this type of compound, O-(2,4-Dichlorobenzyl)hydroxylamine hydrochloride, and friends who are interested can also refer to it.

Reference:
Article; Lv, Xian-Hai; Li, Qing-Shan; Ren, Zi-Li; Chu, Ming-Jie; Sun, Jian; Zhang, Xin; Xing, Man; Zhu, Hai-Liang; Cao, Hai-Qun; European Journal of Medicinal Chemistry; vol. 108; (2016); p. 586 – 593;,
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Application of 1008361-80-5, A common heterocyclic compound, 1008361-80-5, name is 4-Bromo-3-chlorobenzene-1,2-diamine, molecular formula is C6H6BrClN2, 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.

[0660] A mixture of 4-bromo-3-chlorobenzene-1,2-diamine (0.2 g) and oxalic acid (90 mg) in 4N aq. HC1 was refluxed for 5 h. The heterogeneous mixture was then cooled to room temperature and the solid was isolated by filtration. This brick-red solid was washed thoroughly with water and dried under high vacuum. Used as such for the next step (Following the procedure from Organometaiics 2014, 33, 16 17-1622).

The synthetic route of 1008361-80-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAL, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; (394 pag.)WO2017/35360; (2017); A1;,
Chloride – Wikipedia,
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Related Products of 53531-69-4, 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 53531-69-4 as follows.

Step a) Intermediate 204 l-(4-Bromophenyl)-N-methyl-N-(tetrahydro-2H-pyran-4-yl)methanesulfonamide To a suspension of N-methyltetrahydro-2H-pyran-4-amine (0.507 g, 4.40 mmol) and sodium carbonate (0.467 g, 4.40 mmol) in MeCN (10 ml) was added (4- bromophenyl)methanesulfonyl chloride (0.593 g, 2.201 mmol) and the reaction mixture was stirred at r.t. for 1.5 h. The mixture was quenched with water and extracted with EtOAc (x 2). The organics were dried (MgS04) and concentrated under reduced pressure to yield l-(4-bromophenyl)-N-methyl-N-(tetrahydro-2H-pyran-4- yl)methanesulfonamide as a white solid (0.634 g, 83 %). ? NMR (400 MHz, MeOD) delta 7.56 (m, 2H, J = 8.34 Hz), 7.38 (m, 2H, J = 8.34 Hz), 4.34 (s, 2H), 3.95 (dd, 2H, J = 1 1.62, 4.55 Hz), 3.69 – 3.82 (m, 1H), 3.35 – 3.43 (m, 2H), 2.72 (s, 3H), 1.74 – 1.87 (m, 2H), 1.45 – 1.53 (m, 2H)

According to the analysis of related databases, 53531-69-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; RUPRAH, Parminder, Kaur; MERCHANT, Kevin, John; WALSH, Louise, Marie; KERR, Catrina, Morven; FIELDHOUSE, Charlotte; HARRISSON, David; MAINE, Stephanie; HAZEL, Katherine; WO2013/27001; (2013); A1;,
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Electric Literature of 874-17-9, A common heterocyclic compound, 874-17-9, name is 4-Chloro-2,6-dibromoaniline, molecular formula is C6H4Br2ClN, 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.

The RM-1 to RM-10 used for the synthesis of the objective compound are as follows:For the synthesis of the target compound, RM-11 was synthesized by the above reaction scheme.In a round bottom flask, 15.0 g of 2,6-dibromo-4-chloroaniline,(RM-1) were dissolved in 200 ml of 1,4-dioxane, 60 ml of K2CO3 (2M) and 3.64 g of Pd (PPh3) 4 were added, and the mixture was stirred under reflux. After confirming the reaction by TLC, water was added and the reaction was terminated.Then, 13.5 g of phenylboronic acid (RM-1) was dissolved in 200 ml of 1,4-dioxane, 60 ml of K2CO3 (2M) and 41.6 g of Pd (PPh3) were added thereto and the mixture was stirred under reflux. After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with MC, filtered under reduced pressure, and then subjected to column purification to obtain 8 g of intermediate RM-11 (yield 70%).

The synthetic route of 874-17-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DONGJIN SEMICHEM Co., Ltd.; Park Min-su; Ahn Hyeon-cheol; Kang Gyeong-min; Lee Hyeong-jin; Seo Jeong-a; Kim Seung-ho; (76 pag.)KR2019/11090; (2019); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 61881-19-4, name is 2,2,2-Trifluoro-N-phenylacetimidoyl chloride, molecular formula is C8H5ClF3N, 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. Product Details of 61881-19-4

3.1.7 Methyl 4-O-acetyl-2,3-di-O-benzyl-alpha-d-galactopyranosiduronate 1-N-phenyltrifluoroacetimidate (7) Compound 17 (2.40 g, 5.4 mmol) was dissolved in AcOH (90 mL) and Ac2O (90 mL). The reaction mixture was cooled in an ice bath for 10 min, H2SO4 (0.9 mL) was then slowly added. The reaction was monitored by TLC (petroleum ether/ethyl acetate, 2:1) and showed completion after approximately 3 h. The reaction mixture was allowed to warm to rt during the progress of the reaction. NaOAc (9.2 g) was added and the mixture was stirred until all NaOAc had dissolved. The mixture was then evaporated to dryness, taken up in EtOAc, washed with H2O (extracted with EtOAc), dried over Na2SO4, filtered, evaporated to dryness, and finally co-evaporated three times with EtOH. The resulting syrup was purified by chromatography on silica gel (petroleum ether/ethyl acetate, 3:1) to provide a white solid (2.37 g, 93%, alpha and beta isomers were not separable). Ammonia gas was bubbled through a solution of the above product (2.16 g, 4.6 mmol) in a mixture of THF/CH3OH (v/v, 7: 3, 45 mL) cooled in an ice bath for 20 min. The solvent was then concentrated under reduced pressure to give a residue, which was purified by column chromatography on silica gel (petroleum ether/ethyl acetate, 2:1) to afford 18 (1.48 g, 75%) as a white solid. A suspension of hemiacetal 18 (472 mg, 1.1 mmol), K2CO3 (455 mg, 3.3 mmol), and N-phenyl trifluoroacetimidoyl chloride (457 mg, 2.2 mmol) in acetone (6.6 mL) was stirred at ambient temperature for 2 h. TLC showed the completion of the reaction. The mixture was filtered and concentrated in vacuo. The resulting residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate, 7:1) to afford 7 (570 mg, 87%), which was used directly without characterization.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 61881-19-4, its application will become more common.

Reference:
Article; Ma, Yuyong; Cao, Xin; Yu, Biao; Carbohydrate Research; vol. 377; (2013); p. 63 – 74;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics