Author: tianli

Synthetic Route of 1073-39-8, These common heterocyclic compound, 1073-39-8, name is 3-Bromobicyclo[4.2.0]octa-1,3,5-triene, 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.

EXAMPLE 7 Preparation of 1-(4-methylphenyl)-2-(4-benzocyclobutyl)ethene STR23 A solution of 3.0 g 4-bromobenzocyclobutane, 1.9 g 4-methylstyrene, 3.0 g tri-n-butylamine, 150 mg tri-o-tolylphosphine, 36 mg palladium (II) acetate, and 10 ml of acetonitrile is stirred at reflux under nitrogen for 4 hours. The reaction mixture is poured into 60 ml of 10 percent HCl. The product is isolated by filtration, dried, recrystallized from ethanol, and isolated. About 2.9 g of monomer is prepared.

The synthetic route of 1073-39-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The Dow Chemical Company; US4724260; (1988); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 1422-53-3, A common heterocyclic compound, 1422-53-3, name is 2-Bromo-4-fluorotoluene, molecular formula is C7H6BrF, 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.

REFERENCE EXAMPLE 10 To a solution of 2-bromo-4-fluorotoluene (45 g) in dry diethyl ether (500 ml) is added magnesium (for Grignard reagent, 7 g), and the mixture is refluxed with stirring. To the reaction mixture is added methyl iodide (1 ml), by which the reaction initiates vigorously, and then the mixture is stirred for 30 minutes after taking off the heating bath. Thereafter, the reaction becomes mild, and then the reaction mixture is refluxed for 30 minutes. After allowing to cool, dimethyl disulfide (24 ml) is added to the reaction mixture, and the mixture is refluxed for 3 hours. After allowing to cool, water and 10% hydrochloric acid are added to the reaction mixture, and the mixture is extracted with diethyl ether. The extract is washed with water (500 ml*3), dried over anhydrous sodium sulfate and then the solvent is distilled off. The resulting residue is distilled under reduced pressure to give 4-fluoro-2-methylthiotoluene (30 g). b.p. (15 mmHg): 95 C. NMR (CDCl3) delta: 6.60-7.14 (m, 3H), 2.45 (s, 3H), 2.27 (s, 3H)

The synthetic route of 1422-53-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Otsuka Pharmaceutical Company, Limited; US4824834; (1989); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 1073-39-8, A common heterocyclic compound, 1073-39-8, name is 3-Bromobicyclo[4.2.0]octa-1,3,5-triene, molecular formula is C8H7Br, 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.

EXAMPLE 1 Preparation of 1-Phenyl-2-(4-Benzocyclobutyl)ethene STR17 A solution of 2.4 g 4-bromobenzocyclobutane, 1.4 g styrene, 2.4 g tri-n-butylamine, 29 mg palladium (II) acetate, 100 mg of tri-o-tolylphosphine and 10 ml acetonitrile is stirred under nitrogen atmosphere at reflux for three hours. The reaction mixture is poured into 60 ml 10 percent HCl. The product is isolated by filtration, dried, recrystallized in ethanol, and isolated. About 2.10 g of greenish monomer product is prepared.

The synthetic route of 1073-39-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The Dow Chemical Company; US4724260; (1988); 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. 10269-01-9, name is (3-Bromophenyl)methanamine, A new synthetic method of this compound is introduced below., SDS of cas: 10269-01-9

N-(3-Bromobenzyl)-2-(4-fluoro-N-isopropylphenylsulfonamido)acetamide. A 250-mL single- neck round-bottomed flask equipped with a magnetic stirrer was charged with 2-(4-fluoro-N- isopropylphenylsulfonamido)acetic acid (1.0 g, 3.64 mmol), (3-bromophenyl)methanamine (690 mg, 3.64 mmol), HATU (2.76 g, 7.28 mmol), TEA (3 ml), and CH2C12 (50 mL). The mixture was stuffed at room temperature for 2 h and added 2% KHSO4 solution. The resulting mixture was extracted with DCM. The combined organic layer was concentrated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with 3:1 PE/EA to afford the title compound as white solid (960 mg, 60%). MS-ESI: [M+H] 443.1.

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; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BROTHERTON-PLEISS, Christine E.; CHEN, Huifen; CHEN, Shaoqing; CHEN, Zhi; ERICKSON, Shawn David; ESTRADA, Anthony; KIM, Kyungjin; LI, Hongju; LOVEY, Allen John; LYSSIKATOS, Joseph P.; QIAN, Yimin; SO, Sung-Sau; WOVKULICH, Peter Michael; YI, Lin; WO2014/49047; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 54962-75-3,Some common heterocyclic compound, 54962-75-3, name is 3-Bromo-5-(trifluoromethyl)aniline, molecular formula is C7H5BrF3N, 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; Preparation of 3-(trifluoromethyl)-5-(4-methyl-1H-imidazole-1-yl)-benzeneamine of formula I2000 g of 3-bromo-5-trifluoromethylaniline of formula II, 1368 g of 4-methylimidazole of formula III, 181 g of 8-hydroxyquinoline, 238 g of CuI, 666.6 g of NaOH, 933 g of CaO and 7000 ml of DMSO were loaded into a 10 L of 3-neck flask. The reaction mixture was protected with nitrogen and was then stirred at 120 C. 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 45-50 C. and poured into a 50 L reactor. 8.4 L of 14% ammonia was added dropwise and then stirred for 1 hour at 45-50 C. The mixture was cooled down to room temperature. 16.8 L of water and 10 L 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 5 L¡Á3 of 5% of brine for three times. The upper organic layer was separated and dried over 1 kg of anhydrous Na2SO4 overnight. The mixture was filtered and concentrated to obtain 2.3 kg of solid. The residue was dissolved in 2 L of ethyl acetate at 45 C. To the solution was then added 8 L of petroleum ether dropwise at 45 C. The mixture was cooled down slowly to 0-15 C. and stirred for 1 hour. A large amount of precipitate was formed and filtered. The filtered cake was dissolved in 2 L of ethyl acetate at 45 C. The solution was then added 8 L of petroleum ether dropwise at 45 C. The mixture was cooled down slowly to 15-0 C. and stirred for 1 hour. A large precipitate was formed and filtered. The filter cake was dried at 45 C. and 954 g of 3-(trifluoromethyl)-5-(4-methyl-1H-imidazole-1-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.

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

Reference:
Patent; TEVA PHARMACEUTICAL INDUSTRIES LTD.; US2010/16590; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 2862-39-7, 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.

A solution of 5-(2-hydroxyphenyl)-9-[(2R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl]-3,9- diazaspiro[5.5]undecan-2-one (stereoisomer 1) (50.0 mg, 105 pmol) (Example 175) and caesium carbonate (68.4 mg, 210 pmol) in DMF (1 ml_) was was stirred for 10 min at room temperature. Then 2-bromo-N,N-dimethylethan-1 -amine hydrogen bromide (1/1) (24.4 mg, 105 pmol) was added. The mixture was stirred at 80 for 12 hours. The reaction mixture was concentrated in vacuo. The residue was purified via preparative HPLC (method 6) to give the title compound 15.3 mg (95 % purity, 25 % yield).LC-MS (Method 2): Rt= 1.20 min; MS (ESIpos): m/z = 548 [M+H]+Optical rotation (method OR1): +71.1?(methanol).1H-NMR (400 MHz, DMSO-d6) delta [ppm]: 0.390 (0.18), 0.421 (0.34), 0.444 (0.20), 0.763 (0.46), 0.797 (0.44), 0.851 (0.16), 0.894 (0.24), 0.917 (0.40), 0.927 (0.40), 0.950 (0.26), 1.107(1.85), 1.163 (0.62), 1.232 (0.84), 1.269 (0.32), 1.481 (0.62), 1.515 (0.50), 1.899 (0.42), 1.942(0.52), 2.003 (0.64), 2.046 (0.68), 2.121 (0.54), 2.170 (11.10), 2.191 (0.44), 2.225 (16.00), 2.284 (0.58), 2.518 (5.23), 2.522 (3.58), 2.544 (0.50), 2.556 (0.64), 2.570 (0.50), 2.586 (0.54),2.602 (1.49), 2.615 (0.94), 2.629 (1.11), 2.664 (1.15), 2.668 (1.31), 2.673 (1.01), 2.841 (0.30), 2.869 (0.54), 2.908 (0.36), 2.945 (0.58), 2.954 (0.48), 2.967 (0.46), 3.096 (0.30), 3.130 (0.46),3.163 (0.26), 3.244 (0.50), 3.273 (1.15), 3.289 (2.55), 3.367 (0.36), 3.398 (0.24), 3.419 (0.52),3.431 (0.58), 3.446 (0.42), 3.459 (0.36), 3.494 (0.32), 3.513 (0.52), 3.527 (0.60), 3.566 (5.03),3.966 (0.32), 3.976 (0.66), 3.991 (1.39), 4.006 (1 .39), 4.021 (0.72), 4.034 (0.48), 4.050 (0.34), 4.063 (0.18), 4.102 (0.38), 4.135 (0.58), 4.167 (0.24), 4.191 (0.18), 6.716 (0.66), 6.734 (0.76),6.894 (0.30), 6.912 (0.58), 6.931 (0.34), 6.965 (0.54), 6.984 (0.96), 7.004 (1 .75), 7.026 (1 .51 ),7.172 (1 .35), 7.191 (1 .85), 7.219 (1.00), 7.237 (0.76), 7.267 (0.58), 7.285 (1 .93), 7.304 (2.15),7.324 (1 .00), 7.340 (0.66), 7.350 (0.80), 7.358 (0.78), 7.434 (1.97), 7.441 (1 .63), 7.451 (1 .13),7.477 (0.60), 7.495 (0.90), 7.514 (0.40), 7.549 (0.98), 7.554 (1.00), 7.629 (0.66).

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; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; GRAHAM, Keith; BUCHGRABER, Philipp; AIGUABELLA FONT, Nuria; WITTROCK, Sven; HEINRICH, Tobias; BRAeUER, Nico; KUHNKE, Lara, Patricia; LANGE, Martin; BADER, Benjamin; PRECHTL, Stefan; LIENAU, Philip; KOPITZ, Charlotte, Christine; NOWAK-REPPEL, Katrin; POTZE, Lisette; STEUBER, Holger; (754 pag.)WO2020/48831; (2020); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 615-54-3, These common heterocyclic compound, 615-54-3, name is 1,2,4-Tribromobenzene, 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.

Under an argon stream, 340 mg (1.08 mmol) of 1,2,4-tribromobenzene,100 mg (0.0865 mmol) of tetrakis (triphenylphosphine) palladium,And 4.86 mL (4.86 mmol) of 1 M potassium carbonate aqueous solution were dissolved in 12.5 mL of dioxane,And heated to 100 C.Therein was dissolved in 25 mL of dioxane1- [4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl] isoquinoline1.25 g (3.78 mmol) was added dropwise over 3 hours,And the mixture was further stirred for 1 hour.After cooling to room temperature, 400 mL of pure water was added and separation and extraction was performed with chloroform. After distilling off the solvent under reduced pressure, the obtained crude product was purified by silica gel column chromatography (developing solvent: chloroform: ethyl acetate = 7: 3)4 ‘- [4- (1-isoquinolyl) phenyl] -1,1’: 2 ‘, 1 “- terphenylOf pale yellow solid (yield 536 mg, yield 72.2%).

Statistics shows that 1,2,4-Tribromobenzene is playing an increasingly important role. we look forward to future research findings about 615-54-3.

Reference:
Patent; TOSOH CORPORATION; FUJITA, KANA; ARAI, NOBUMICHI; NOMURA, KEISUKE; IIDA, TAKASHI; TANAKA, TSUYOSHI; (76 pag.)JP6264877; (2018); B2;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 10016-52-1, The chemical industry reduces the impact on the environment during synthesis 10016-52-1, name is 2,8-Dibromodibenzo[b,d]furan, I believe this compound will play a more active role in future production and life.

In a 25 ml four-necked flask, 0.52 g (2.0 mmol) of 4-phenylaminodibenzofuran, 0.33 g (1.0 mmol) of 2,8-dibromodibenzofuran, 500 mg (5.2 mmol) of sodium t-butoxide, 10 ml of dehydrated toluene In addition, nitrogen bubbling was performed for 1 hour. after that,Pd2 (dba) 392 mg (0.10 mmol),After adding 58 mg (0.20 mmol) of tri-t-butylphosphonium tetrafluoroborate, the mixture was heated under reflux for 12 hours while stirring under a nitrogen stream. The formation of the desired product was confirmed by TLC and MS. The reaction solution was cooled to room temperature, and the organic layer was extracted with toluene, washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated to obtain a brown viscous product. The resulting gum was dissolved in 5 ml of toluene and loaded onto the column. The crude product was directly purified by silica gel column chromatography (developing solvent: toluene / hexane = 1/4) to obtain 0.51 g of the target product HTM5 in a yield of 75%.

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, 2,8-Dibromodibenzo[b,d]furan, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; National University Corporation Yamagata University; Sasabe, Hisahiro; Kido, Junji; Kamata, Takahiro; (21 pag.)JP2019/26556; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 103273-01-4,Some common heterocyclic compound, 103273-01-4, name is 2-Bromo-4-(tert-butyl)aniline, molecular formula is C10H14BrN, 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.

Step 2: Synthesis of 2-amino-3′,5-di-t-butylbiphenyl 3-t-butylphenylboronic acid (4.0 g, 22.4 mmol), 2-bromo-4-t-butylaniline (4.3 g, 18.7 mmol), palladium(II) acetate (0.11 g, 0.468 mmol), triphenylphosphine (0.5 g, 1.8 mmol) and was added 2 M solution of potassium carbonate in 25 of ethylene glycol dimethyl ether in the 36 . The reaction mixture was heated under reflux for 18 hours. Cool the reaction to room temperature, and separating the aqueous phase from the organic phase. The aqueous phase was extracted with ethyl acetate. The organic extracts were combined, dried over magnesium sulfate, filtered and concentrated. It was purified by column chromatography using 20% ethyl acetate and hexane the crude product as an eluent. Collected as a pure product of 2-amino-3 ‘, 5-di -t- butyl biphenyl (3.0 g, 57% yield) of a white solid, and its NMR is consistent with the proposed structure.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-4-(tert-butyl)aniline, its application will become more common.

Reference:
Patent; UNIVERSAL DISPLAY CORPORATION; NOLIS, DAVID B; LIN, CHOOK; MCKINSEY, PETER BODON; CHAI, CHUI LEE; WALTERS, ROBERT W; PIERS, SCOTT A; BROWN, CORY S; IGOR, WALTER H; (101 pag.)KR2016/30582; (2016); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 65896-11-9,Some common heterocyclic compound, 65896-11-9, name is 2-Bromo-6-fluoroaniline, molecular formula is C6H5BrFN, 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 2A Methyl (2E)-3-[2-amino-3-fluorophenyl]propenoate Starting with 42.00 g (221.04 mmol) of 2-bromo-6-fluoroaniline, the general procedure [B] gives 29.66 g (68% of theory) of product. HPLC (method 1): Rt=4.14 min MS (ESIpos): m/z=196 (M+H)+

The synthetic route of 65896-11-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer HealthCare AG; US2007/185121; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary