Month: May 2021

875664-38-3, name is 1-Bromo-4,5-difluoro-2-methylbenzene, 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. Application In Synthesis of 1-Bromo-4,5-difluoro-2-methylbenzene

4′,5′-Difluoro-2′-methyl-biphenyl-4-ol To a stirred solution of 3,4-difluorotoluene (30 g, 234.1 mmol) and iron powder (0.784 g, 14.05 mmol) in methylene chloride (140 mL) in an ice bath was added bromine (12 mL, 155 mmol) slowly over 6.5 hrs. The reaction mixture was warmed to RT and stirred for an additional 60 hrs. The mixture was washed with water (200 mL), 10% Na2SO3 (3*150 mL), saturated (NaHCO3 (100 mL) and saturated NaCl. The organic layer was dried over MgSO4, filtered and concentrated in vacuo to give 40 g of crude 1-bromo-4,5-difluoro-2-methyl-benzene. Bromo-4,5-difluoro-2-methyl-benzene (30 g, 145 mmol) and 4-hydroxyphenyl-boronic acid (20.99 g, 152.2 mmol) were suspended in 725 ml of dioxane. The mixture was degassed with argon. Potassium carbonate (23.17 g, 166 mmol) in 72.5 ml water solution was added and after stirring for 10 minutes, bis(tricyclohexylphosphine)palladium(0) (2.4 g, 3.62 mmol) was added. The reaction was stirred at 80-85 C. for 19 hrs and concentrated. The mixture was diluted with ethyl acetate and water. The organic layer was washed with brine, dried and solvents were evaporated. The crude product was purified by flash chromatography, eluting with 0-7% ethyl acetate in hexanes to obtain the crude product which was further recrystallized from hexane to afford 4′,5′-difluoro-2′-methyl-biphenyl-4-ol (23.76 g, 74.5%). LR-MS (ES) calculated for C13H10F2O, 220.22. found m/z 219 [M-H].

The synthetic route of 875664-38-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bolin, David Robert; Hamilton, Matthew Michael; McDermott, Lee Apostle; Qian, Yimin; US2011/112158; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 1260850-70-1, A common heterocyclic compound, 1260850-70-1, name is 3-Bromoimidazo[1,2-b]pyridazin-6-ylamine, molecular formula is C6H5BrN4, 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.

3-bromoimidazo[l,2-b]pyridazin-6-amine (1.8 g, 7.0 mmol), 2-fluorophenylboronic acid (1.33 g,7.0 mmol), Cs2C03 (4.57 g, 14.0 mmol) and Pd[PPh3]4 (0.4 g,0.35 mmol) were dissolved in a mixture solvent (dioxane:water:ethanol = 4: 1 : 10 drops). The reaction was stirred at 100 C for about 4 h. The mixture was purified on a silica gel column to give 3- (2-fluorophenyl)imidazo[l,2-b]pyridazin-6-amine (1.05 g,55%). MS (ESI) calcd for

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; SIRTRIS PHARMACEUTICALS, INC.; BLUM, Charles, A.; SPRINGER, Stephanie, K.; VU, Chi, B.; WO2013/59589; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 5279-32-3, A common heterocyclic compound, 5279-32-3, name is 5,6-Dibromobenzo[d][1,3]dioxole, molecular formula is C7H4Br2O2, 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: A 12 mL vial was charged with Pd(OAc)2 (2 mol%), BuPAd2 (6 mol%), and a stirring bar. Then, 2 ml dioxane and 1 mmol of bromobenzene were injected by syringe. The vial (or several vials) was placed in an alloy plate, which was transferred into a 300 mL autoclave of the 4560 series from Parr Instruments under argon atmosphere. After flushing the autoclave three times with NH3, a pressure of 2 bar NH3 and 2 bar CO was adjusted at ambient temperature. Then, the reaction was performed for 16 hours at 100 oC. After the reaction is finished, the autoclave was cooled down to room temperature and the pressure was released carefully. Then, CuI (5 mol%), DMEDA (10%), K2CO3 (3 mmol) and 1,2-dibromobenzene were added in under air, the vial was closed and heated to 110oC for 20 hours. The reaction mixture cooled down to room temperature. The solution was extracted 3-5 times with 2-3 ml of ethyl acetate from aqua solution. After evaporation of the organic solvent the residue was adsorbed on silica gel and the crude product was purified by column chromatography using n-heptane/AcOEt (20:1) as eluent.

The synthetic route of 5279-32-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wu, Xiao-Feng; Neumann, Helfried; Neumann, Stephan; Beller, Matthias; Tetrahedron Letters; vol. 54; 24; (2013); p. 3040 – 3042;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 4102-60-7, 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. 4102-60-7 name is 18-Bromo-6,9-octadecadiene, 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.

Intermediate 127b: (6Z,9Z)-18-iodooctadeca-6,9-diene To a solution of intermediate 127a (14.0 g, 42.659 mmol) in acetone (150 mL) in a RBF charged with a magnetic stir bar under N2 was added sodium iodide (12.7 g, 85.3 mmol). The reaction was heated to reflux (55 C) for 2 hours, after which it was cooled to room temperature and the solids were filtered off. The solvent was evaporated and the remaining solids were removed by dissolution in H20 (100 mL) and extraction with DCM (2 x 200 mL). The combined organic layers were dried over Na2S04 and evaporated to dryness to afford the desired product as a crude pale brown liquid (15.5 g, 97%). This material was used in the next step without further purification. TLC: Rf = 0.6 (100% pentane), PMA active.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 18-Bromo-6,9-octadecadiene, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; BRITO, Luis; CHEN, Delai; GAMBER, Gabriel Grant; GEALL, Andrew; LOVE, Kevin; ZABAWA, Thomas; ZECRI, Frederic; WO2015/95346; (2015); 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. 105309-59-9, name is Tetrakis(4-bromophenyl)methane, A new synthetic method of this compound is introduced below., HPLC of Formula: C25H16Br4

B is prepared according to the procedure described in reference 5.[0186] A 250 mL Schlenk flask was charged with A (4g, 6.3 mmol), B (6.79 g, 37.7 mmol), CsF (9.5 g, 63.9 mmol),and Pd(P(Ph)3)4 0.3 g. 120 ml DME was degassed and transferred. A water condenser was then equipped. The flaskwas heated to reflux under the nitrogen for 48 hours. The solvent was dried on rotary evaporator. The residue wasdissolved by CH2Cl2, and purified by column chromatography to get C 4.1g (Yield. 76%).

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; THE TEXAS A&M UNIVERSITY SYSTEM; Zhou, Hong-Cai; Feng, Dawei; Wang, Kecheng; EP2876112; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 1257535-06-0, name is 3-Bromo-4-fluorobenzene-1,2-diamine, 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. Computed Properties of C6H6BrFN2

A 500 mL round-bottomed flask charged with 3-bromo-4-fluorobenzene-l,2-diamine (18 g, 88 mmol), DMF (100 mL), ethyl 2-bromopropionate (Sigma Aldrich, 1 1.54 mL, 89 mmol) and NaHC03, powder (7.60 g, 90 mmol) was heated to 90 C with a reflux condenser for 30 min, then at 120 C for 15 h. The reaction was cooled to RT, treated with brine and extracted with EtOAc (2 x 200 mL), washed with brine (3 x) and dried over Na2S04, filtered and concentrated affording crude 8-bromo-7-fluoro-3-methyl-3,4- dihydroquinoxalin-2(lH)-one (21.75 g, 84 mmol, 96 % yield) as an orange-brown viscous oil. The material was used in the subsequent step without further purification: FontWeight=”Bold” FontSize=”10″ H NMR (400 MHz, DMSO-d6) delta ppm 9.67 (s, 1 H) 6.78 – 6.89 (m, 1 H) 6.48 – 6.78 (m, 1 H) 6.07 – 6.35 (m, 1 H) 1.25 (d, J=6.46 Hz, 3 H). 19F NMR (377 MHz, DMSO-d6) delta ppm -120.49 (1 F, s). m/z (ESI, +ve ion) 259.0/261.0 (M+H)+.

The synthetic route of 3-Bromo-4-fluorobenzene-1,2-diamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; CEE, Victor J.; BROWN, James; CHAVEZ JR., Frank; CHEN, Jian J.; HERBERICH, Bradley J.; HARRINGTON, Essa Hu; LANMAN, Brian Alan; LEE, Matthew; PETTUS, Liping H.; REED, Anthony B.; TASKER, Andrew; WANG, Hui-Ling; WU, Bin; WURZ, Ryan; WO2014/22752; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 1071449-08-5, name is 7-Bromo-2,3-dihydro-1H-inden-1-amine, 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 1071449-08-5, Recommanded Product: 7-Bromo-2,3-dihydro-1H-inden-1-amine

To a solution of 7-bromo-2,3-dihydro-1 H-inden-1 -amine (ACS Med. Chem. Lett. 201 1 , 2, 565-570) (346 mg, 1 .63 mmol) and 3-(1 -(fe/ -butoxycarbonyl)piperidin-4-yl)-2-ethylpyridine 1 – oxide (250 mg, 0.816 mmol) and DIPEA (143 muIota_, 0.816 mmol) in CH2CI2 (5ml_), was added PyBrOP (761 mg, 1 .632 mmol). The reaction was stirred at room temperature for 76 h. The reaction was quenched with 1 N citric acid solution. The bi-layer was then separated. The aqueous layer was extracted twice with CH2CI2. The combined organic layers were washed with brine and dried over Na2S04, filtered, and then concentrated. The resulting residue was absorbed onto silica gel, and purified by silica gel flash column chromatography (0 to 60% EtOAc in CH2CI2) to afford the title compound. MS (ESI+) m/z 499.9 (M+H).

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, 7-Bromo-2,3-dihydro-1H-inden-1-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; ADAMS, Christopher Michael; BEVAN, Doug; CAPPARELLI, Michael Paul; EHARA, Takeru; FERRARA, Luciana; JI, Nan; KATO, Mitsunori; MAINOLFI, Nello; MEREDITH, Erik; MOGI, Muneto; POWERS, James J.; PRASANNA, Ganesh; (226 pag.)WO2016/1875; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 875664-41-8, These common heterocyclic compound, 875664-41-8, name is 3-Bromo-4,5-difluoroaniline, 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.

3-bromo-4,5-difluoroaniline (2.6 g, 12.8 mmol) in toluene (20 mL) was added dropwise to a solution of 4-chlorosulfonyl-1-methyl-pyrrole-2-carbonylchloride (3100 mg, 12.8 mmol) in toluene (160 mL) at reflux. The reaction mixture was refluxed 2 hours and next allowed to cool to room temperature.

The synthetic route of 875664-41-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN R&D IRELAND; VANDYCK, Koen; HACHE, Geerwin, Yvonne, Paul; LAST, Stefaan, Julien; MC GOWAN, David, Craig; ROMBOUTS, Geert; VERSCHUEREN, Wim, Gaston; RABOISSON, Pierre, Jean-Marie, Bernard; WO2014/184350; (2014); 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. 60956-23-2, name is 1,2-Dibromo-4-methylbenzene, A new synthetic method of this compound is introduced below., Computed Properties of C7H6Br2

General procedure: Into a dried two-necked flask (50 mL) equipped with a condenser were placed a stirrer bar, Mg powder (99.9%, 24 mmol), LiCl (24mmol), DMI (20 mL), and chlorodimethylsilane (48 mmol). After stirring the mixture at rt for 15 min, 1,2-dibromoarene (3 mmol) was added and the mixture was stirred for 4 h. The mixture was quenched with sat. NaHCO3 and the resulting precipitates were filtered off. The filtrate was extracted with hexane (3 ×) and the combined organic extract was washed with brine, dried (anhyd Na2SO4), and concentrated by a rotary evaporator. The crude product was purified by column chromatography (silica gel, hexane or hexane/CH2Cl2).

The synthetic route of 60956-23-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kitamura, Tsugio; Yamada, Rin; Gondo, Keisuke; Eguchi, Nobuo; Oyamada, Juzo; Synthesis; vol. 49; 11; (2017); p. 2495 – 2500;,
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. 1171381-49-9, name is (4-Bromo-2-methylphenyl)methanamine hydrochloride, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: (4-Bromo-2-methylphenyl)methanamine hydrochloride

[00371] Step 1. To a stirred mixture of (4-bromo-2-methylphenyl)methyl amine hydrochloride 92-A (160 mg, 0.68 mmol) and triethyl amine (207 mg, 2.04 mmol) in 10 mL of CH2CI2 at room temperature was added acid chloride 1-B (170 mg, 0.88 mmol). Reaction was continued for 2h, and the mixture was concentrated. The residue was purified by preparative TLC to provide amide intermediate 92-B as a colorless solid (150 mg, 62%). 1H NMR (400 MHz, CDC13) delta: .35-126 (m, 3H), 7.21 (d, J = 8.4 Hz, 2H), 7.04 (t, J = 8.4 Hz, 1H), 5.88 (br, 1H), 4.61 (d, J = 5.6 Hz, 2H), 2.37 (s, 3H). LC-MS: m/z = 356.0 [M+H]+.

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 1171381-49-9.

Reference:
Patent; BIOGEN IDEC MA INC.; CHAO, Jianhua; ENYEDY, Istvan, J.; GUERTIN, Kevin; HUTCHINGS, Richard, H.; JONES, John, Howard; POWELL, Noel; VANVLOTEN, Kurt, D.; WO2014/8214; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary