Author: Jessica.F

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. 49764-63-8, name is 4,5-Dibromobenzene-1,2-diamine, A new synthetic method of this compound is introduced below., Safety of 4,5-Dibromobenzene-1,2-diamine

General procedure: To a 10 mL vial were added o-diaminobenzene 2 (0.2 mmol, 1.0 equiv), DIPEA(0.24 mmol, 1.2 equiv), and toluene (2 mL), followed by the slow addition of a solution of-acetoxy allenoate 1 (0.24 mmol,1.2 equiv) in toluene (2 mL). The solution was stirred for 12 h atroom temperature. The reaction mixture was concentrated under reduced pressure, and the residuewas purified by silica gel column chromatography using petroleum ether and ethyl acetate (30:1 to15:1 v/v) as the eluent to give the corresponding annulations product 3.

The synthetic route of 49764-63-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Yi-Fan; He, Cheng-Yu; Hou, Longlei; Tian, Ping; Lin, Guo-Qiang; Tong, Xiaofeng; Synlett; vol. 29; 9; (2018); p. 1176 – 1180;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 103-64-0, name is (2-Bromovinyl)benzene, 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 103-64-0, Quality Control of (2-Bromovinyl)benzene

beta-Bromostyrene (7 mL, 54.57 mmol) was dissolved in 64 mL Et2O and cooled to -78 C. t-BuLi (1.6M in pentane, 64 mL, 102.4 mmol) was added over 40 min. The mixture was stirred at -78 C for 1 h, at which time (R)-7-allyl-3-isobutoxy-7-methylcyclohept-2-enone (4, 7.8335 g, 33.14 mmol) in 15 mL Et2O was added by cannula with a 5 mL rinse. After 90 min, the reaction was warmed with an ice bath and stirred for 1 h. The reaction was quenched with 10% HCl (100 mL), and the volatiles removed in vacuo. To the residue was added 100mL THF. The mixture was then heated to 50 C for 12 h. After cooling to room temperature, the mixture was extracted 4 * 100mL Et2O. The combined organic extracts were dried over MgSO4, and evaporated in vacuo. Silica gel chromatography (5 * 17 cm, ~700 mL 20:1 hexanes:EtOAc then~1.6 L 15:1 hexanes:EtOAc) afforded the title compound as a viscous yellow oil (8.0542 g, 91% yield). RF = 0.23 (10:1 Hexane:EtOAc); 1H NMR (300 MHz, CDCl3) delta 7.45-7.27 (m, 5H), 6.90 (s, 2H), 6.31 (s, 1H), 5.68 (dddd, J = 6.6, 8.1, 10.5, 17.1 Hz, 1H), 5.09-5.01 (m, 2H), 2.66-2.61 (m, 2H), 2.47 (dd, J = 6.6, 14.1 Hz, 1H), 2.14 (dd, J 8.1,14.1 Hz, 1H), 1.93-1.80 (m, 3H), 1.70-1.60 (m, 1H), 1.27 (s, 3H); 13C NMR (125 MHz, CDCl3) delta 204.5, 158.3, 136.5, 133.7, 133.1, 129.0, 128.7, 128.3, 126.9, 126.9, 118.3, 46.0, 44.3, 44.2, 38.5, 26.6, 17.4; IR (Neat Film NaCl) 3075, 3026, 2925, 1640, 1582, 1450, 1344, 1250,1217, 963, 916, 752, 694 cm-1; HRMS m/z calc’d for C19H22O [M]+: 266.1671, found 266.1668; [alpha]D24.8 +33.70 (c 1.19, CHCl3, 88% ee).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (2-Bromovinyl)benzene, and friends who are interested can also refer to it.

Reference:
Article; Harned, Andrew M.; Stoltz, Brian M.; Tetrahedron; vol. 75; 24; (2019); p. 3166 – 3177;,
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. 2635-13-4, name is 5-Bromobenzo[d][1,3]dioxole belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: bromides-buliding-blocks

General procedure: A 25mL Schlenk tube was charged with Cu2O(0.05mmol),ArX (0.5mmol), NHR1R2(0.75mmol), NaOH (1mmol),TBAB (0.1mmol), L1 (0.1mmol) and water (1mL). Themixture was stirred at 130C for 24h. The reaction mixturewas extracted with ethyl acetate (3 × 10mL), washed withwater and brine, dried over anhydrous Na2SO4,and concentratedin vacuo. The residue was purified by flash columnchromatograph on silica gel (ethyl acetate/petroleum etheras the eluent) to provide the target products 3a-3w.

The synthetic route of 2635-13-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Xiaochuang; Meng, Fei; Zhang, Jie; Xie, Jianwei; Dai, Bin; Catalysis Letters; vol. 148; 4; (2018); p. 1142 – 1149;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 1422-54-4,Some common heterocyclic compound, 1422-54-4, name is 2-Bromo-6-fluorotoluene, molecular formula is C7H6BrF, 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 187 6-(3-Fluoro-2-methylphenyl)-1,2-dihydro-2,2,4-trimethylquinoline (Compound 287, structure 4 of Scheme II, where R1 =3-fluoro-2-methylphenyl) This compound was prepared by General Method 2 (EXAMPLE 9) from Compound 9 (50 mg, 0.158 mmol) and 2-bromo-6-fluorotoluene (60 mg, 0.315 mmol). Purification by flash chromatography on silica gel (20 g) using 5% EtOAc:hexanes afforded 6 mg (14%) of Compound 287 as a yellow oil.

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-6-fluorotoluene, its application will become more common.

Reference:
Patent; Ligand Pharmaceuticals Incorporated; US5696130; (1997); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 58458-10-9, name is 3-Amino-2-bromobenzotrifluoride, 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 58458-10-9, Product Details of 58458-10-9

A mixture of 2-bromo-3-(tri r1uoromethyl)benzenamine (9.6 g; 40 mmol), 3,6-dihydro- 4-(4.4.5.5-tetramethyl- 1.3.2-dioxaborolan-2-yl )- 1.1-dimethylethylester- 1(2H)- pyridinecarboxilic acid (14.84 g; 48 mmol ). [l. l “-bis|bis( 1.1- dimethylethyl )phosphinoJferrocene]dichloro-palladium (652 mg; 1 mmol) and sodium carbonate (16.96 g; 160 mmol) in water (100 ml .) and THF (300 ml, ) was heated at reflux overnight. The solvent was removed under reduced pressure and the residue was solubilized with EtOAc and H20. The organic layer was separated, dried over MgSO.i, filtered and evaporated. The residue was purified by chromatography over silica gel (eluent: from 100% petrol ether to 50% petrol ether, 50% EtOAc). The pure fractions were collected and the solvent was evaporated to give 12 g (95%, white crystals) of intermediate 152

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

Reference:
Patent; JANSSEN PHARMACEUTICA NV; MEVELLEC, Laurence, Anne; MEERPOEL, Lieven; COUPA, Sophie; PONCELET, Virginie, Sophie; PILATTE, Isabelle, Noelle, Constance; PASQUIER, Elisabeth, Therese, Jeanne; BERTHELOT, Didier, Jean-Claude; QUEROLLE, Olivier, Alexis, Georges; MEYER, Christophe; ANGIBAUD, Patrick, Rene; DEMESTRE, Christophe, Gabriel, Marcel; MERCEY, Guillaume, Jean, Maurice; (302 pag.)WO2016/97347; (2016); 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. 5279-32-3, name is 5,6-Dibromobenzo[d][1,3]dioxole, A new synthetic method of this compound is introduced below., Quality Control of 5,6-Dibromobenzo[d][1,3]dioxole

Preparation of 5-(6-bromobenzo[d][1,3]dioxol-5-yl)pyrazin-2-amine (15).; Palladium tetrakis-triphenylphosphine (31 mg, 30 mumol) was added to a degassed solution of dibromide 10 (150 mg, 54 mumol) and boronate 14 (130 mg, 59 mumol) in dioxane:acetonitrile:water (9:9:2, 2.7 mL) and potassium carbonate (171 mg, 800 mumol). The resulting mixture was heated under argon at 90 C. with stirring for 2 h. The mixture was then cooled, diluted with dichloromethane (10 mL), dried with sodium sulfate and concentrated under reduced pressure. Flash chromatography (ISCO system, silica, 0-50% ethyl acetate in hexane) provided 15 (19.6 mg, 12%) as a solid: LRESIMS m/z 294.1 [M+H]+, calcd. for C11H9Br1N3O2 294.0.

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; CalciMedica, Inc.; US2011/263612; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

114078-88-5, name is 5-Bromo-1,2,3-triazine, 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. Quality Control of 5-Bromo-1,2,3-triazine

To a solution of 5-bromotriazine (20.0 g, crude) in 1,4-dioxane (600 mL) was added pyrimidine-2-carboxamidine (16.8 g, 137.53 mmol) at 0 C. After being stirred at 0 C for 1 hrs, the resulting mixture was warmed to 30 C and stirred at 30 C for 1 hr, and then filtered. The filtrate was concentrated in vacuo. The residue was diluted with H20 (500 mL) and extracted with DCM (500 mL) for three times. The combined organic layer was washed with brine (1.0 L), dried over anhydrous Na2S04 and concentrated in vacuo. The residue was purified on silica gel column (eluting with DCM/MeOH= 10/1, v:v) to give 5-bromo-2-pyrimidin-2-yl-pyrimidine (9.0 g) as yellow solid.

The synthetic route of 114078-88-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; WANG, Jianhua; WANG, Min; YANG, Song; (81 pag.)WO2018/83136; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 2695-48-9, A common heterocyclic compound, 2695-48-9, name is 8-Bromo-1-octene, molecular formula is C8H15Br, 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.

A suspension of Mg (30.6 mg, 1.26 mmol) and 8-bromo-1-octene (0.20 mL, 1.19 mmol) in THF (10 mL) was stirredat 50C. After being stirred for 1 h, Mg solid was perfectlyconsumed. To a solution of 9 (0.11 mL, 1.00 mmol) and NiCl2(16.3 mg, 0.0300 mmol) in THF (5.0 mL) was added the prepared7-octenylmagnesium bromide at 0C and the mixturewas stirred at room temperature for 1 h. After the additionof sat. NH4Cl aq. (30 mL) at 0C, the reaction mixture wasextracted with EtOAc (10 mL × 3), dried over MgSO4, andconcentrated under reduced pressure. The residue was purifiedby silica gel column chromatography (hexane-EtOAc = 5 : 1)to afford 7 (67.6 mg, 0.290 mmol, 29%) as a colorless oil.

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:
Article; Kutsumura, Noriki; Inagaki, Mai; Kiriseko, Akito; Saito, Takao; Chemical and Pharmaceutical Bulletin; vol. 67; 6; (2019); p. 594 – 598;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 6911-87-1,Some common heterocyclic compound, 6911-87-1, name is 4-Bromo-N-methylaniline, molecular formula is C7H8BrN, 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.

[00347] Step 1. To a stirred solution of 4-bromophenyl methyl amine 63-A (0.098 mL, 0.78 mmol) in 5 mL of CH2CI2 was added triethyl amine (0.217 mL, 1.55 mmol) followed by 2- chloro-6-fluoro-benzoyl chloride 1-B (0.116 mL, 0.881 mmol). The reaction mixture was stirred at room temperature overnight. The mixture was diluted with ethyl acetate, and then washed with a sat. NaHC03 aqueous solution, H20, and brine. The organic layer was dried over anhydrous Na2S04. Solvents were removed in vacuo, the residue was purified by gradient column chromatography eluting with EtOAc / Heptanes to give the amide intermediate 63-B (270 mg, 100%). LC-MS: m/z = 341.9 [M+H]+.

The synthetic route of 6911-87-1 has been constantly updated, and we look forward to future research findings.

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

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 3344-70-5 as follows. Recommanded Product: 3344-70-5

General procedure: A dibromoalkane (1 equiv.) and sodium azide (3 equiv.) were dissolved in 4 : 1 DMF/H2O (15 mL). The mixture was irradiated in a CEM microwave reactor at 125oC (200 W, 200 psi) for 3 h. The reaction mixture was then cooled to room temperature, and 2-ethynylpyridine (2 equiv.), sodium ascorbate (0.5 equiv.), and CuSO4*5H2O (0.4 equiv.) were added to the reaction mixture. The mixture was stirred at room temperature for 12 h. The suspension was partitioned between aqueous 0.1M NH4OH/ethylenediaminetetraacetic acid (EDTA) (100 mL) and CH2Cl2 (100 mL), and the layers were separated. The organic phase was washed with water (100 mL) and brine (100 mL), dried over MgSO4, and the solvent was removed under reduced pressure to provide the ligands as off-white solids.

According to the analysis of related databases, 3344-70-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kumar, Sreedhar V.; Lo, Warrick K. C.; Brooks, Heather J. L.; Hanton, Lyall R.; Crowley, James D.; Australian Journal of Chemistry; vol. 69; 5; (2016); p. 489 – 498;,
Bromide – Wikipedia,
bromide – Wiktionary