Month: February 2021

Related Products of 348-57-2, 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.

EXAMPLE 17 Preparation of 4-(2,4-difluorophenyl)-anisole from 4-methoxyphenylmagnesiumbromide and palladium acetate/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 acetate (0.00663 g; 0.0295 mmoles–Janssen) and triphenylphosphine (0.03074 g; 0.1172 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 (92percent yield).

Statistics shows that 1-Bromo-2,4-difluorobenzene is playing an increasingly important role. we look forward to future research findings about 348-57-2.

Reference:
Patent; Zambon Group S.p.A.; US5312975; (1994); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 18087-73-5, A common heterocyclic compound, 18087-73-5, name is 3-Bromoimidazo[1,2-b]pyridazine, molecular formula is C6H4BrN3, 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 28; N-[ (1R,6S)-6-Amino-2,2-difluorocyclohexyl]-5-chloro-4-(imidazo[1,2-b]pyridazin-3-yl)-1,3- thiazole-2-carboxamide; Step 1. 1 -(Imidazo[1,2-b]pyridazin-3-yl)ethanone; 3-Bromoimidazo[1,2-b]pyridazine (1.0 g, 5.05 mmol), tributyl(l-ethoxyvinyl)tin (3.41 mL, 10.1 mmol), and PdCb(PPh3)2 (354 mg, 0.505 mmol), were added to a sealed tube. DMF (25.2 mL) was added and the reaction purged with nitrogen for 5 minutes. The reaction was heated at 100 C for 18 h. The reaction was cooled to room temperature and quenched with aqueous saturated sodium bicarbonate. The aqueous layer was extracted with ethyl acetate (x 3) and the combined organic layers were dried with magnesium sulfate, Filtered, and concentrated under reduced pressure. The residue was diluted with methanol (10 mL) and HCl in 1,4-dioxane (1.26 mL, 5.05 mmol, 4M) was added. The solution was stirred at room temperature for 1 h. The reaction was then quenched with aqueous saturated sodium bicarbonate and extracted with ethyl acetate (x 3). The combined organic layers were dried with magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography to afford the title compound. 1H NMR (500 MHz, CD3SOCD3) delta 8.76 (d, 1H); 8.55 (s, 1H); 8.31 (d, 1H); 8.49 (dd, 1H); 2.64 (s, 3H). LRMS (APCI) calc’d for (C8H7N3O) [M+H]+, 162.1; found 162.1.

The synthetic route of 18087-73-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP &; DOHME CORP.; ALTMAN, Michael, D.; BILODEAU, Mark, T.; LIM, Jongwon; NORTHRUP, Alan; STANTON, Matthew, G.; TAOKA, Brandon, M.; WO2010/83145; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 1073-39-8, name is 3-Bromobicyclo[4.2.0]octa-1,3,5-triene, 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 1073-39-8, Quality Control of 3-Bromobicyclo[4.2.0]octa-1,3,5-triene

To a mixture of 3-bromobicyclo[4.2.0]octa-1 (6),2,4-triene (300 mg, 1.64 mmol, 1.10 equiv) in THF (4 mL) was added n-BuLi (2.5 M in hexane, 0.66 mL, 1.64 mmol, 1.00 equiv) dropwise at -78C. The reaction mixture was stirred for 30 min at -78C. To the resulting mixture was then added a solution of 4- (benzyloxy)-5-bromo-2-(dimethylamino)benzaldehyde (500 mg, 1.50 mmol, 1.00 equiv) in THF (1 mL) dropwise at -78 C. The reaction mixture was stirred for 3 h at -78C. NH4CI/H2O was added and the mixture was extracted with EtOAc thrice. The combined extracts were washed with brine and dried over Na2S04, then concentrated and purified by chromatography on silica gel (3: 1 PE/EA) to yield (4-(benzyloxy)-5-bromo-2-(dimethylamino)phenyl)(1,2- dihydrocyclobutabenzen-4-yl)methanol as a colorless oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Bromobicyclo[4.2.0]octa-1,3,5-triene, and friends who are interested can also refer to it.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; GAUL, Micheal; KUO, Gee-Hong; XU, Guozhang; LIANG, Yin; (218 pag.)WO2018/89449; (2018); 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. 53398-55-3, name is 1-Bromo-3,5,7-trimethyladamantane, A new synthetic method of this compound is introduced below., HPLC of Formula: C13H21Br

Example 6: l-Acetamido-3.5.7-dirnethyladamantane (Ac-NH-TMAD) synthesis; 4 g of l-bromo-3,5,7-trimethyladamantane, 12 g (15 ml) of acetonitrile, and 7 g of 75% phosphoric acid are added to a 50ml reactor equipped with condenser, mechanical stirrer, thermometer at 20-250C and under nitrogen. After addition, the internal temperature rises to 30-320C. The obtained biphasic system is warmed to 87+/-2C over about 30 min (slight reflux) and the temperature maintained for 17 hrs. During the course of the reaction, a monophasic system is obtained. At this point, the reaction is complete. n-butanol (15ml), toluene (15ml) and water (15ml) are added and the resulting biphasic system is cooled to 20-250C. Sodium hydroxide 30% is added to reach pH 6-7 and the temperature rises to 40-450C. Phases are separated at 35-400C and the aqueousphase is discarded. Water (15ml) is loaded to the organic phase and, after stirring and standing, the phases are separated at 40-45. The organic phase is concentrated under vacuum (res. pressure 45-50 mmHg, external temperature 80-850C, internal temperature 40-700C) until a residual volume of 6-6.5ml is obtained. After cooling to 55-600C, acetone (30ml) is added. The resulting suspension is warmed to reflux (62-63C) until complete dissolution is obtained. After cooling to 500C, water (50ml) is slowly added and crystallization of l-acetamido-3,5,7-dimethyladamantane occurs. After 1.5-2hrs at 18+/-3C, the solid is filtered, washed with water and dried at 45-500C for 15hrs. Dry weight: 3.3g 1H NMR is reported: 1H-NMR in CDCl3 (298K)

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; TEVA PHARMACEUTICAL FINE CHEMICALS S.R.L.; TEVA PHARMACEUTICALS USA, INC.; WO2007/126886; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 91319-54-9, 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. 91319-54-9, name is 1-(2-Bromoethyl)-2-fluorobenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 134 Synthesis of 1-[1-(2-fluorophenethyl)piperidin-4-yl]-6-acetamidomethylindoline 1-(Piperidin-4-yl)-6-acetamidomethylindoline (250 mg) and 2-fluorophenethyl bromide (220 mg) were treated as in Example 2 to give the title compound (190 mg) as a white-powder (yield: 52%). m.p.: 160-161 C. 1H-NMR (400 MHz, CDCl3): delta(ppm) 1.51-1.68(2H, m), 1.81-1.92(2H, m), 2.00(3H, s), 2.20-2.40(2H, m), 2.70-2.89(4H, m), 2.91(2H, t, J=8Hz), 3.01-3.10(2H, m), 3.40-3.48(3H, m), 4.32(2H, d, J=6Hz), 6.39(1H, s), 6.51(1H, d, J=8Hz), 6.98-7.10(3H, m), 7.18-7.30(2H, m). FAB-Mass: 396(MH+).

The synthetic route of 1-(2-Bromoethyl)-2-fluorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eisai Co., Ltd.; US2002/19531; (2002); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 19190-91-1, A common heterocyclic compound, 19190-91-1, name is 5,6-Dibromo-1,2-dihydroacenaphthylene, molecular formula is C12H8Br2, 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.

General procedure: Dibromoarene 1 (0.5 mmol), alkyne 2 (0.6 mmol), Pd(OAc)2 (5 mol%, 5.6 mg ),Xantphos (5.5 mol%,16 mg), K2CO3 (1.5 mmol, 207 mg) were added into a Schlenkflask. The flask was evacuated and backfilled with nitrogen (3 cycles). Dry DMF (5mL) was added by syringe. The mixture was heated to 120 C and stirred until thereaction finished (TLC analysis). After cooling to room temperature, the mixture wasextracted three times with ethyl acetate. The organic layers were combined and driedover Na2SO4. After filtration, the solvents were evaporated. The crude product wasfurther purified by silica gel chromatography, using petroleum ether and ethyl acetateas eluents to provide the pure product

The synthetic route of 19190-91-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; An, Wenbo; Li, Gaoqiang; Ma, Jun; Tian, Youping; Xu, Feng; Synlett; vol. 25; 11; (2014); p. 1585 – 1590;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 10016-52-1, 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. 10016-52-1, name is 2,8-Dibromodibenzo[b,d]furan belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(3) Synthesis of Compound (300) [0266] [0267] Into a three-necked flask, 3.80 g (10.2 mmol) of Compound (300-b), 1.39 g (4.25 mmol) of Compound (291-a), 15 ml of a 2 M aqueous solution of sodium carbonate, 30 ml of 1,2-dimethoxyethane, and 0.368 g (0.425 mmol)) of Pd(PPh3)4 were charged, and the contents were refluxed for 12 h in a nitrogen atmosphere. [0268] After the reaction, the reaction solution was added with 100 ml of methanol and ultrasonically washed for 10 min. The precipitate was separated by filtration and washed with methanol, water, and then hexane. The washed precipitate was dried, dispersed in ethyl acetate for washing, and recrystallized from toluene, to obtain a white solid. The identification was based on the molecular weight measurement by FD/MS, which showed m/e = 654 for the molecular weight of 654. The yield was 1.50 g and the percent yield was 54%.

The synthetic route of 2,8-Dibromodibenzo[b,d]furan has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Idemitsu Kosan Co., Ltd; NAKANO, Yuki; NUMATA, Masaki; NAGASHIMA, Hideaki; EP2711363; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 1647-23-0, 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. 1647-23-0, name is 1-Bromo-3,3-dimethylbutane belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

The title compound was prepared from 50 mg 3-ter/-butylquinolin-2(lH)-one (Preparative Example 1, Step E), 55 mg l-bromo-3,3-dimethylbutane, and 143 mg cesium carbonate in 1 mL DMF at 55C for 12 hours. It was separated from less polar side-product 3-ter*-butyl-2-(3,3-dimethylbutoxy)-7- methoxyquinoline using RP-etaPLC. The isomers were identified by comparison of NMR with isomers in Preparative Example 1, Step F. 1H NMR in CDCl3 at 500 MHz: 7.53 (s, IH), 7.46 (d, 9.0 Hz5 IH), 6.81 (dd, 9.0 & 2.0 Hz, IH), 6.77 (d, 2.0 Hz, IH), 4.29 (m, 2H), 3.92 (s, 3H), 1,68 (m, 2H)5 1.44 (s, 9H), 1.26 (s, 9H).

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, 1-Bromo-3,3-dimethylbutane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK & CO., INC.; WO2007/108968; (2007); A2;,
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. 134168-97-1, name is 3-Bromo-5-fluoroaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: bromides-buliding-blocks

1000mL 4 neckround bottom flask was charged with 3-bromo-5-fluoroaniline 30.5 g (0.16 mole) and Pd (PPh3) 47.4 g (0.006mole) of potassium carbonate and 88.1 g (0.64 mole) and 3-pyridineboronic acid 23.4 put g (0.19 mole), toluene was put into210 mL, 160 mL ethanol, 90 mL of water was refluxed for 12 hours. To complete the reaction, and the organic layer wasseparated and the water layer was extracted twice with 100 mL toluene. Formed organic layer was concentrated underreduced pressure and recrystallized with methanol to intermediate 6a(21.1 g, 70.0%) was obtained.

The synthetic route of 134168-97-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SFC CO., LTD.; KIM, JEONG SOO; RYU, YEON KWON; KO, SANG WON; LEE, SU JIN; KIM, JI HWAN; PARK, JIN JOO; (44 pag.)KR2015/129486; (2015); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 445303-69-5,Some common heterocyclic compound, 445303-69-5, name is 4-Bromo-2-(difluoromethyl)-1-fluorobenzene, molecular formula is C7H4BrF3, 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 10 mL microwave vial was added 4-(4-fluorophenyl)-l-(l-methyl-lH-imidazol-4- ylsulfonyl)pyrrolidin-3 -amine hydrochloride (100 mg, 0.277 mmol) and premixed tris(dibenzylidene- acetone)dipalladium(0)/sodium tert-butoxide/ 2,2′-bis(diphenylphosphino)-l ,1 ‘-binaphthyl (100 mg, 0.05:0.15:2), aldrich 715530). The solids were suspended in 1 ,2-dimethoxyethane, and 4-bromo-2- (difluoromethyl)-l -fluorobenzene (74.8 mg, 0.333 mmol) was added. The reaction vessel was capped and the reaction mixture was heated in a microwave (Biotage Initiator, maximum 400 Watts) for 15 min at 130C. The mixture was filtered through celite, concentrated, dissolved in 2 ml 50% methanol/dimethylsulfoxide, and purified by HPLC to provide the title compound. MS (ESI) m/z 469 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-2-(difluoromethyl)-1-fluorobenzene, its application will become more common.

Reference:
Patent; ABBVIE DEUTSCHLAND GMBH & CO. KG; ABBVIE INC.; AMBERG, Wilhelm; POHLKI, Frauke; LANGE, Udo; WANG, Ying X.; ZHAO, Hongyu H.; LI, Huan-Qiu; BREWER, Jason T.; ZANZE, Irini; DIETRICH, Justin; VASUDEVAN, Anil; DJURIC, Stevan, W.; LAO, Yanbin; HUTCHINS, Charles W.; WO2014/140310; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary