Month: February 2021

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

These common heterocyclic compound, 348-57-2, name is 1-Bromo-2,4-difluorobenzene, 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: 1-Bromo-2,4-difluorobenzene

EXAMPLE 19 Preparation of 4-(2,4-difluorophenyl)-anisole from 4-methoxyphenylmagnesiumbromide and palladium chloride/triphenylphosphine (0.05percent) A suspension of magnesium turnings (1.54 g; 63.3 mmoles-Pometon) in tetrahydrofuran (16.02 g) was heated at 65¡ã C. under stirring and under nitrogen. Then, iodine (0.02 g) and, after 30 minutes, 4-bromoanisole (11.69 g; 62.5 mmoles), in 1 hour, were added to the reaction mixture. At the end of the addition, the reaction mixture was kept at 75¡ã C. for 1 hour and, then, decanted obtaining a solution of 4-methoxyphenylmagnesiumbromide (solution A). A mixture of 1-bromo-2,4-difluorobenzene (11.4 g; 59.1 mmoles), palladium chloride (0.00526 g; 0.0297 mmoles–Fluka) and triphenylphosphine (0.03088 g; 0.1177 mmoles–Fluka) was de-aerated by vacuum/nitrogen at 25¡ã C. The mixture was heated at 85¡ã C., kept under stirring for 15 minutes and, then, solution A was added in 3 hours. At the end of the addition, the reaction mixture was kept at 85¡ã C. for 30 minutes. After cooling at 60¡ã C., a solution of 37percent hydrochloric acid (2 ml) in water (10 ml) was added in 20 minutes. The mixture was cooled at 40¡ã C. and the phases were separated. The solvent of the organic phase was evaporated under reduced pressure obtaining the desired compound (98.5percent yield).

The synthetic route of 1-Bromo-2,4-difluorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zambon Group S.p.A.; US5312975; (1994); A;,
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 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

Related Products of 2550-36-9, 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. 2550-36-9, name is (Bromomethyl)cyclohexane, This compound has unique chemical properties. The synthetic route is as follows.

4-(4-chlorophenyl)-1 -(2-methoxyethyl)-6-methyl-2-oxo-3,4-dihydropyridine-5-carboxylic acid (example 74, 75 mg, 0.23 mmol) was dissolved in anhydrous DMF (1 mL) then cesium carbonate (1 14 mg, 0.35 mmol) and cyclohexylmethylbromide (49 muIota_, 0.35 mmol) were added. The reaction mixture was stirred at 50 C for 24 h. The solvent was removed under reduced pressure. The residue was dissolved in EtOAc and water. The aqueous phase was extracted with EtOAc. The organic layers were assembled, washed with brine and dried over MgS04. The solvent was removed under reduced pressure to give the desired [cyclohexylmethyl 4-(4- chlorophenyl)-1 -(2-methoxyethyl)-6-methyl-2-oxo-3,4-dihydropyridine-5-c a r b o x y l a t e a s a yellowish oil (95 mg, 99 %). 1 H N MR (300 MHz, CDCI3) delta 0.71 -1 .18 (m, 5H), 1 .46-1 .63 (m, 6H), 2.61 (s, 3H), 2.71 (dd, J = 15.7, 2.3 Hz, 1 H), 2.92 (dd, J = 15.7, 7.5 Hz, 1 H), 3.32 (s, 3H), 3.38 (ddd, J = 9.8, 8.5, 3.7 Hz, 1 H), 3.47 (dt, J = 9.8, 3.9 Hz, 1 H), 3.75 (ddd, J = 14.6, 8.5, 3.9 Hz, 1 H), 3.81 -3.91 (m, 2H), 4.13-4.21 (m, 2H), 7.1 1 (d, J = 8.5 Hz, 2H), 7.22 (d, J = 8.5 Hz, 2H). MS [M+H]+ 420. HRMS : calcd for C23H3i N04CI, [M+H]+ 420.1942, found 420.1937.

The chemical industry reduces the impact on the environment during synthesis (Bromomethyl)cyclohexane. I believe this compound will play a more active role in future production and life.

Reference:
Patent; UNIVERSITE DE LILLE 2 DROIT ET SANTE; INSTITUT PASTEUR DE LILLE; INSERM (INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE); CHARTON, Julie; DEPREZ, Benoit; LEROUX, Florence; STAELS, Bart; MUHR-TAILLEUX, Anne; HENNUYER, Nathalie; LESTAVEL, Sophie; PICON, Sylvain; AKNIN, Karen; BOULAHJAR, Rajaa; DUBANCHET, Barbara; (234 pag.)WO2016/16238; (2016); 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

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. 201138-91-2, name is 4,6-Dibromodibenzo[b,d]furan belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: bromides-buliding-blocks

General procedure: The triolborate, dibromides (0.2 mmol), palladium acetate (10 mol %), BIPHEP (11 mol), and CuCl (0.4 equiv) were placed in a flask under an atmosphere of nitrogen. DMF (15 mL) was added, and heated at 80 C for 14 h. After cooling to room temperature, 15 mL water was added, extracted with dichloromethane, dried over MgSO4, and then purified by chromatography on silica gel.

The synthetic route of 201138-91-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Li, Gao-Qiang; Yamamoto, Yasunori; Miyaura, Norio; Tetrahedron; vol. 67; 36; (2011); p. 6804 – 6811;,
Bromide – Wikipedia,
bromide – Wiktionary

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

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. 327-51-5, name is 1,4-Dibromo-2,5-difluorobenzene, A new synthetic method of this compound is introduced below., HPLC of Formula: C6H2Br2F2

Synthesis of H2 (p-F2-bdp). H2(p-F2-bdp) was prepared via a Suzuki-Miyaura coupling as generally depicted in Scheme 3. Specifically, 1,4-dibromo-2,5-difluorobenzene (2.18 g, 8.0 mmol, 1.0 equiv), 1-(2-tetrahydropyranyl)-1H-pyrazole-4-boronic acid pinacol ester (5.56 g, 20.0 mmol, 2.5 equiv), and K3PO4 (8.48 g, 40 mmol, 5 equiv) were suspended in toluene (16 mL) in a 40-mL glass scintillation vial with a magnetic stir bar and sparged with Ar for 10 minutes. XPhos Pd G2 (1.26 g, 1.6 mmol, 0.2 equiv) was added quickly in air, and vial was briefly purged with Ar, sealed with a PTFE-lined cap, and heated to 110 C. while stirring for 2 days. Upon completion, the reaction mixture was cooled to room temperature, concentrated under reduced pressure, and diluted with 250 mL of diethyl ether. The ether layer was washed 5 times with 250 mL of saturated aqueous NaHCO3 solution, dried over MgSO4, and concentrated under reduced pressure to yield a yellow oil, which was used in the subsequent reaction without additional purification. The crude ligand was dissolved in 60 mL of methanol in a 250-mL round-bottom flask with a magnetic stir bar, 12 mL of concentrated aqueous HCl was added, and the reaction mixture was stirred at 50 C. for 2 h, during which time a white precipitate formed. The reaction mixture was filtered, and the filtrate was suspended in water and neutralized with NaHCO3. The precipitate was again isolated by filtration, washed with water, and dried in vacuo to yield H2(p-F2-bdp) (0.86 g, 3.5 mmol, 44%) as a beige powder. 1H NMR (400 MHz, DMSO-d6): delta 8.11 (s, 4H), 7.68 (t, J=9.3 Hz, 2H) ppm; 13C NMR (101 MHz, DMSO-d6): delta 156.06, 153.68, 132.40, 119.33-119.81 (m), 118.58-118.14 (m), 114.60-113.78 (m) ppm; 19F NMR (400 MHz, DMSO-d6): delta -119.78 (t, J=9.3 Hz) ppm. Note that the 1H NMR signals from the hydrogen atoms bonded to the pyrazole nitrogen atoms are too broad to be visible. Anal. Calcd. for C12H8F2N4: C, 58.54, H, 3.27, N, 22.75; found: C, 57.72, H, 3.35, N, 21.82. IR: 3139 (m), 3076 (w), 2966 (m), 2938 (m), 2850 (m), 1589 (m), 1539 (w), 1490 (m), 1435 (w), 1374 (m), 1350 (w), 1273 (m), 1241 (w), 1155 (s), 1041 (m), 963 (s), 867 (s), 818 (m), 780 (s), 698 (m), 668 (w), 605 (s), 549 (w), 531 (w), 512 (w), 482 (w), 472 (w), 460 (m) cm-1.

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

Reference:
Patent; The Regents of the University of California; Long, Jeffrey R.; Mason, Jarad A.; Taylor, Mercedes K.; Oktawiec, Julia; (70 pag.)US2018/297010; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 13633-25-5, These common heterocyclic compound, 13633-25-5, name is 1-Bromo-4-phenylbutane, 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.

4-bromophenol (8.6 g, 49.9 mmol), 4-phenylbutyl bromide (11.2 g, 52.6 mmol) and potassium carbonate (13.7 g, (40 ml) was added under stirring with N, N-dimethylformamide (40 ml). The reaction was heated to reflux and refluxed at reflux conditions The reaction was carried out for 2 hours. The reaction solution was cooled to room temperature, water (160 ml) was added, and the mixture was extracted with ether (100 ml x 2) to combine the organic phases. The organic phase was washed successively with 0.5 M sodium hydroxide solution (110 ml) and water (110 ml), dried over anhydrous sodium sulfate and filtered to remove The filtrate was concentrated under reduced pressure and the concentrate was purified by silica gel chromatography to give 11.3 g of the title compound in 74.3% yield.

The synthetic route of 13633-25-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Beijing Haibu Pharmaceutical Technology Co., Ltd.; Di Wei; Sun Fengqing; (17 pag.)CN107253903; (2017); A;,
Bromide – Wikipedia,
bromide – Wiktionary