Tag: M.W=200-300

40161-54-4, name is 1-Bromo-2-fluoro-4-(trifluoromethyl)benzene, 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. name: 1-Bromo-2-fluoro-4-(trifluoromethyl)benzene

(1) A suspension of Compound 1 (590 muL), Compound 2 (3162 muL), and potassium carbonate (1191 mg) in N-methylpyrrolidone (3 mL) was heated under microwave radiation at 180C for 2 hours. The reaction solution was cooled to room temperature, poured into water, and then extracted with ethyl acetate. The resultant organic layer was washed with water and saturated saline, dried, and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane:ethyl acetate=99:1-90:10) to give Compound 3 (3.336 g) as a colorless viscous material. MS (ESI): m/z 380/382 [M+H] +

The synthetic route of 40161-54-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; YAMAMOTO, Yasuo; SATO, Atsushi; MOROKUMA, Kenji; SHITAMA, Hiroaki; ADACHI, Takashi; MIYASHIRO, Masahiko; (260 pag.)EP3150578; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 176317-02-5, name is 1-Bromo-2,3,4-trifluorobenzene, 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 176317-02-5, Quality Control of 1-Bromo-2,3,4-trifluorobenzene

EXAMPLE 207 1,2-Dihydro-2,2,4-trimethyl-6-(2,3,4-trifluorophenyl)quinoline (Compound 307, structure 4 of Scheme II, where R1 =2,3,4-trifluorophenyl) This compound was prepared by General Method 2 (EXAMPLE 9) from compound 9 (60 mg, 0.19 mmol) and 1-bromo-2,3,4-trifluorobenzene (0.11 mL, 0.93 mmol). The crude product was purified by silica gel chromatography (EtOAc/hexane, 10:1) to afford 30 mg (53%) of Compound 307 as white crystals. Data for compound 307: 1 H NMR (400 MHz, acetone-d6) 7.28 (m, 1H), 7.20 (m, 2H), 7.13 (dt, J=8.2, 1.9, 1H), 6.58 (d, J=8.3, 1H), 5.43 (br s, 1H), 5.39 (s, 1H), 2.00 (d, J=1.3, 3H), 1.30 (s, 6H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-2,3,4-trifluorobenzene, and friends who are interested can also refer to it.

Reference:
Patent; Ligand Pharmaceuticals Incorporated; US5688810; (1997); A;; ; Patent; Ligand Pharmaceuticals Incorporated; US5693647; (1997); A;; ; Patent; Ligand Pharmaceuticals Incorporated; US5696127; (1997); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 75024-22-5,Some common heterocyclic compound, 75024-22-5, name is 1,4-Dibromo-2,3-dimethylbenzene, molecular formula is C8H8Br2, 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 1 Synthesis Method of Exemplary Compound A-l Exemplary Compound A-l was synthesized according to the synthesis scheme described below.; (1) Synthesis of Intermediate 1; The following reagents and solvent were placed into a reaction vessel.1, 4-dibromo-2 , 3-dimethylbenzene : 5.00 g (18.94 mmol) N-bromosuccinimide (NBS) : 7.41 g (41.63 mmol)Anhydrous carbon tetrachloride: 100 ml[0090] Next, the mixture was stirred to dissolve the solid matters, and then the following reagent was placed into the reaction vessel.Benzoyl peroxide (BPO) : 30 mg (0.12 mmol)[0091] Next, the reaction solution was stirred for 5 hours while being heated under reflux. Next, after the reaction solution was left standing to cool, insoluble matters were filtered out, and the solvent contained in the filtrate was distilled away under reduced pressure to thereby obtain a crude product. Next, the crude product was purified by a silica gel columnchromatography (developing solvent: toluene), thereby obtaining 2.98 g (yield: 37%) of Intermediate 1.

The synthetic route of 75024-22-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CANON KABUSHIKI KAISHA; OKAJIMA, Maki; YAMADA, Naoki; WO2011/40631; (2011); 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. 13633-25-5, name is 1-Bromo-4-phenylbutane, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 13633-25-5

To a stirred solution of tert-Butylprop-2-yn-1-ylcarbamate (300 mg, 1.93 mmol, 1 eq.) in dry DMF (1.93 mL) under nitrogen at 0C, was added NaH (93 mg, 60% in oil, 2.32 mmol, 1.2 eq.) in small portions. After stirring for 15min, (4-bromobutyl)benzene (410 muL, 2.34 mmol, 1.2 eq.) was added dropwise followed by KI(32 mg, 0.19 mmol, 0.1 eq.) and the reaction was warmed up to room temperature for 15 h.After completion of the reaction, water and brine were added and the aqueous layer wasextracted with Et2O (three times). Then, the combined organic layers were dried over MgSO4,filtered and concentrated under vacuum. The crude residue was purified by flash columnchromatography on silica gel (cyclohexane/DCM: 50/50) to afford 1h (446 mg, 1.54 mmol, 80%)as a colorless oil. 1H NMR (300 MHz, CDCl3): delta 7.31-7.24 (m, 2H), 7.21-7.14 (m, 3H), 4.01 (br. s,2H), 3.33 (t, J = 6.6 Hz, 2H), 2.64 (t, J = 7.1 Hz, 2H), 2.16 (t, J = 2.4 Hz, 1H), 1.67-1.56 (m, 4H),1.45 (s, 9H); 13C NMR (100 MHz, CDCl3): delta 155.2 (br. s), 142.4 (br. s), 128.5 (2C), 128.4 (2C),125.8, 80.2, 80.0 (br. s), 71.4 (br. s), 46.4, 36.4 and 36.0 (br. S, rot.), 35.6, 28.6 (br. s), 28.5 (3C),27.6 (br. s).

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 13633-25-5.

Reference:
Article; Guissart, Celine; Dolbois, Aymeric; Tresse, Cedric; Saint-Auret, Sarah; Evano, Gwilherm; Blanchard, Nicolas; Synlett; vol. 27; 18; (2016); p. 2575 – 2580;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 18392-81-9,Some common heterocyclic compound, 18392-81-9, name is 5,6-Dibromobenzo[c][1,2,5]thiadiazole, molecular formula is C6H2Br2N2S, 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 mixture of N,N?-1,3-bis(2,6-diisopropylphenyl)imidazolium chloride [51] (0.45 g, 1.06 mmol) and Pd(OAc)2 (0.13 g, 0.59 mmol) in toluene (4mL), a suspension of NaOt-Bu (0.16g, 1.66mmol) in dry toluene (3mL) was added under inert conditions. The solution was heated at 88C for 30min. This mixture was cooled to room temperature and added to a pressure tube containing 2 [41] (2.00g, 6.8mmol) in toluene (70mL). To this mixture, tert-butylamine (1.5mL, 14.27mmol) was added followed by NaO-tBu (1.60g, 16.65mmol). The pressure tube was sealed and heated for 16hat 130C. After cooling, the reaction mixture was filtered through Celite. The filtrate was collected and evaporated to yield 3 as a light brown solid (1.941g, crude yield). The crude product was engaged in the following reaction with no further purification. 1H NMR (CDCl3, 300MHz): delta 7.14 (s, 2H, ArH), 3.40 (br, 2H, NH), 1.41 (s, 18H, CH3).

The synthetic route of 18392-81-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tapu, Daniela; Buckner, Ossie J.; Boudreaux, Chance M.; Norvell, Bradley; Vasiliu, Monica; Dixon, David A.; McMillen, Colin D.; Journal of Organometallic Chemistry; vol. 823; (2016); p. 40 – 49;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 393-37-3, 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 393-37-3 as follows.

General procedure: Example 3Tandem Borylation/Dehalogenation of 1-Chloro-4-fluoro-3-Substituted- and 1-Bromo-4-fluoro-3-Substituted BenzenesTandem borylation/dehalogenation was also investigated as a strategy for the ortho-borylation of arenes that are substituted with an electron-withdrawing group. The scheme below illustrates the tandem borylation/dehalogenation methodology which was investigated. As discussed above, in the case of arenes that are substituted with an electron-withdrawing group, iridium-catalyzed C-H activation-borylation of the arene is typically governed by steric effects. In tandem borylation/dehalogenation, the substrate can include an electron-withdrawing group and a sacrificial atom (e.g., a halogen such as Cl or Br) positioned para to the electron-withdrawing group, so as to sterically hinder attack of the iridium catalyst at the otherwise sterically favored position meta to the electron-withdrawing group. As a result, iridium-catalyzed C-H activation-borylation of the arene exclusively generates the ortho-borylated (electronic) product. Subsequent dehalogenation can afford exclusively the desired electronic product.[0337] General Procedure for Borylation [0338] In a nitrogen atmosphere glovebox B2Pin2 (140 mg, 0.55 mmol) was weighed into a 20 mL vial containing a magnetic stir bar. [Ir(OMe)cod]2 (6.6 mg, 0.02 mmol) and 4,4?-di-tert-butyl-2,2?-dipyridyl ligand (5.4 mg, 0.02 mmol) were weighed into two separate test tubes, each being diluted with THF (2 mL). The [Ir(OMe)cod]2 solution was transferred into the 20 mL vial containing B2Pin2. This mixture was stirred until a golden yellow clear solution was obtained. The solution containing ligand was transferred into the vial, and the mixture was stirred until it became a dark brown color solution. The substrate (1 mmol) was added to the vial, which was then sealed. The reaction mixture stirred for 24 h at rt, after which the vial was removed from the glovebox. The reaction mixture was passed through a short plug of silica eluting with a 10:1 hexane/EtOAc solution (2¡Á10 mL). The volatiles were removed by rotary evaporation affording the product, which was characterized using standard methodologies. 4-Bromo-1-fluoro-2-(trifluoromethyl)benzene was borylated using the general procedure described above. The borylation reaction afforded product as colorless oil (0.229 g, 62%): 1H NMR (500 MHz, CDCl3) delta 8.02 (dd, J=2.5, 3.5 Hz, 1H), 7.78 (dd, J=2.5, 6.5 Hz, 1H), 1.36 (s, 12H); 13C NMR (125 MHz, CDCl3) delta 162.9 (dd, J=1.9, 259.7 Hz), 143.1 (d, J=8.5 Hz), 132.8 (qd, J=1.9, 4.7 Hz), 121.7 (q, J=270.3 Hz), 120.0 (qd, J=33.1, 16.1, Hz), 116.3 (d, J=3.5 Hz), 84.7, 24.8; 19F NMR (470 MHz, CDCl3) delta 61.9, 106.4; 11B NMR (160 MHz, CDCl3) delta 29.3 (br s).

According to the analysis of related databases, 393-37-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Smith, III, Milton R.; Maleczka, JR., Robert E.; Li, Hao; Jayasundara, Chathurika; Oppenheimer, Jossian; Sabasovs, Dmitrijs; US2015/65743; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 113170-72-2, A common heterocyclic compound, 113170-72-2, name is 3-Bromo-5-(trifluoromethyl)benzene-1,2-diamine, molecular formula is C7H6BrF3N2, 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 8 : 7-brom -2-(6-fluoropyridin-3 -yl)-5 -(trifluoromethyl)- 1 H-benzimidazole To a mixture of 6-fluoronicotinaldehyde (2.5 g, 19.98 mmol), 3-bromo-5-(trifluoromethyl)benzene-l,2-diamine (4.84 g, 19.98 mmol) in DMF (40 ml) and water (4 ml) added potassium peroxymonosulfate (7.99 g, 12.99 mmol) in portions over 1 hour. The reaction mixture was stirred overnight under N2 then pour into water (50 ml), extract with 3×80 ml ethyl acetate. The organic layers were combined, washed with 2×25 ml of saturated brine, dried over anhydrous sodium sulfate and concentrated under vacuum. Part of the product was crystallized from dichloromethane. The mother liquor was purified by reverse phase HPLC to afford 7- bromo-2-(6-fluoropyridin-3-yl)-5 -(trifluoromethyl)- 1 H-benzimidazole as brown solid. LC-MS (ES, m/z) Ci3H6BrF4N3 : 361; Found: 362 [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; INTERVET INTERNATIONAL B.V.; DE VITA, Robert, J.; HONG, QingMei; LAI, Zhong; DYKSTRA, Kevin, D.; YU, Yang; LIU, Jian; SPERBECK, Donald; JIAN, Tianying; GUIADEEN, Deodial; XU-QIANG YANG, Ginger; WU, Zhicai; HE, Shuwen; TING, Pauline, C.; ASLANIAN, Robert; KUETHE, Jeffrey, T.; BALKOVEC, James, M.; KUANG, Rongze; ZHOU, Gang; WU, Heping; WO2012/164071; (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. 203302-95-8, name is 4-Bromo-3,5-difluoroaniline, This compound has unique chemical properties. The synthetic route is as follows., category: bromides-buliding-blocks

4-bromo-3, 5-difluoroaniline (500 mg, 2.4 mmol), 2-trifluoromethoxybenzeneboronic acid (590 mg, 2.9 mmol), Pd2(dppf)Cl2 (98 mg, 0.12 mmol), cesium carbonate (2.35 g, 7.2 mmol) and acetonitrile/water (10 mL/1 mL) were added to a microwave tube. The mixture was nitrogen sparged for 5 min, stirred and heated to 120 C for 1 hour under microwave, washed with saturated ammonium chloride (20 mL), and separated by silica gel column (petroleum ether: ethyl acetate = 50:1) to give the product of 2,6-difluoro-2?-trifluoromethoxy-[1,1?-biphenylyl]-4-amine (yellow oil, 460 mg), with a yield of 66.3%. 1H NMR (400 MHz, CDCl3) delta 7.47-7.28 (m, 4H), 6.29-6.27 (d, J= 9.1Hz, 2H), 3.67 (s, 2H). MS (ESI) m/z: 290.1 (MH+).

According to the analysis of related databases, 203302-95-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Fudan University; WANG, Yonghui; HUANG, Yafei; YU, Fazhi; TANG, Ting; EP3476829; (2019); A1;,
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. 4549-33-1, name is 1,9-Dibromononane belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C9H18Br2

General procedure: To a stirred solution of 2-(phenylsulfonyl)methyl-4,5-diphenyloxazole 1 (500 mg, 1.33 mmol, 1.0 equiv) in dry THF (10 mL) was added potassium tert-butoxide (1.60 mmol, 1.2 equiv) at 5 C. The resulting yellow reaction mixture was stirred under a nitrogen atmosphere (30 min). The dibromo alkane (1.60 mmol, 1.2 equiv) was then slowly added to the reaction mixture by syringe, and reaction mixture was allowed to warm to room temperature and stirring was continued (16 h). After completion of reaction, cold water (10 mL) was poured into the reaction mixture followed by extraction with dichloromethane (2 x 20 mL). The organic layers were combined, washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude residue was submitted to gravity-column chromatography (hexane/ethyl acetate, 9:1) to afford the corresponding products 2a-d.

The synthetic route of 4549-33-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Patil, Pravin C.; Luzzio, Frederick A.; Tetrahedron; vol. 73; 29; (2017); p. 4206 – 4213;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 2635-13-4, name is 5-Bromobenzo[d][1,3]dioxole, 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 2635-13-4, Product Details of 2635-13-4

Step 1a. 5-Bromo-6-iodobenzo[d][1,3]dioxole (Compound 0102-1) A solution of 5-bromobenzo[d][1,3]dioxole (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).

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, 5-Bromobenzo[d][1,3]dioxole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Cai, Xiong; Qian, Changgeng; US2010/184801; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary