Category: bromides-buliding-blocks

Synthetic Route of 58971-11-2,Some common heterocyclic compound, 58971-11-2, name is 3-Bromophenethylamine, molecular formula is C8H10BrN, 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 stirred solution of 2-(3-bromophenyl)ethanamine (500mg) and tetrakis(triphenylphosphine)palladium(0) (60mg) in pyrrolidine (4ml) under nitrogen, was added a solution of (5R)-3-[6-(but-3-ynyloxy)hexyl]-5-(2,2-dimethyl4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one (example 1 vi) (912mg) in pyrrolidine (4ml) and the reaction mixture was heated to 80C. After 18h, water (10ml) was added and extracted with EtOAc (3x25ml), the combined organic layers dried (MgSO4) and the solvent removed in vacuo. The residue was dissolved in CH2Cl2 (25ml) and applied to a Biotage cartridge (40g) and eluted with CH2Cl2, EtOAc and CH2Cl2 : EtOH: aq NH3 (100 : 8 : 1) to give the title compound (668mg). LCMS RT=3.09min.

The synthetic route of 58971-11-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2003/72539; (2003); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 328-70-1, 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. 328-70-1, name is 1-Bromo-3,5-bis(trifluoromethyl)benzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A three-neck round bottom flask fitted with a reflux condenser was evacuated, flame dried and filledwith argon prior to use. 1.01 g (41.7 mmol) magnesium, 0.72 g (6.4 mmol, 1 eq) NaBF4 and diethylether (150 mL) were added. To start to reaction 1.07 g (0.49 ml, 5.7 mmol, 0.9 eq) dibromoethanewere added and the flask was heated for several minutes followed by the dropwise addition of 1.71 g(6.25 ml, 36 mmol) 3,5-bis(trifluoromethyl)bromobenzene diluted with diethyl ether (50 mL) over30 min. When the exothermic reaction slowed the reaction mixture was heated for additional 30 min.The solution was then stirred over night at room temperature. The reaction mixture was quenched bythe addition of 16 g Na2CO3 in distilled water (200 mL), stirred for 30 min and filtered. The aqueousphase was extracted three times with diethyl ether (50 mL), the combined organic phases were driedover sodium sulfate and charcoal followed by filtration. The solvent was removed and the remainingcrude product was dissolved in toluene (200 mL) to remove the water with a Dean Stark trap byazeotropic distillation. The solvent was removed, the product filtered, washed with dry toluene anddried under vacuo. The product was observed as colorless solid (4.65 g, 5.3 mmol, 82 %).m.p. decomposition >290 C.1H-NMR (300 MHz, DMSO-d6): delta = 7.67 (s, 4H, B-p-CH), 7.61 (s, 8H, B-o-CH) ppm.13C-NMR (75.5 MHz, DMSO-d6): delta = 161.0 (q, JB = 50 Hz, 4 Ci-B), 134.0 (s, 8 B-o-CH), 128.5 (qq,JF = 31 Hz, JB = 2.7 Hz, 8 Ci-CF3), 124.0 (q, JF = 272 Hz, CF3), 117.6 (m, 4 B-p-CH) ppm.19F-NMR (283 MHz, DMSO-d6): delta = -57.6 (CF3) ppm.Elemental analysis for C32H12BF24Na*1.8 H2O: calcd. C = 41.61 H = 1.70, found C = 41.57, H = 1.66.

The synthetic route of 1-Bromo-3,5-bis(trifluoromethyl)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kaliner, Maria; Strassner, Thomas; Tetrahedron Letters; vol. 57; 31; (2016); p. 3453 – 3456;,
Bromide – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 1003-99-2, name is 2-Bromo-5-fluoroaniline, 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 1003-99-2, Quality Control of 2-Bromo-5-fluoroaniline

2-Azido-l-bromo~4-fluorobenzene. 2-Bromo-5-fluoro aniline (2.00 g, 10.53 mmol) was dissolved in concentrated HCl (10 mL) and water (10 mL) and cooled to 0 °C. Aqueous NaNO2 solution (1.090 g, 15.8 mmol OfNaNO2 in 10 mL of water) was added dropwise at such a rate that the temperature did not exceed 5°C. This mixture was stirred at 00C for 1.5 h. A solution OfNaN3 (1.027 g, 15.8 mmol) and NaOAc (12.95 g, 158 mmol) in water (50 rnL) was then added at 0-5°C and the mixture was stirred for an additional Ih at this temperature. The mixture was extracted with ethyl acetate and the combined extracts were washed with brine and dried over Na2SO4. The filtrate was concentrated to afford the title compound as a tan solid (2.188 g, 96percent): 1H NMR (400 MHz, CDCl3): 7.53 (1 H, dd, J=8.8, 5.6 Hz), 6.94 (1 H, dd, J=8.8, 2.8 Hz), 6.79 (1 H, ddd, J=8.8, 7.6, 2.8 Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-5-fluoroaniline, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2007/64316; (2007); A1;,
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. 454-79-5, name is 2-Bromo-5-(trifluoromethyl)aniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 454-79-5

General procedure: To a stirred solution of 2-haloaniline derivatives in DCM, Et3N (1.3 equiv.) was added and the resulting mixture was cooled to 0 C. Stirred for 5 min and acid chloride (1.1 equiv.) was added drop wise. Stirred overnight from 0 C to RT. The reaction mixture was extracted with DCM and washed with NaHCO3 and brine. The organic phase was dried over anhydrous sodium sulphate and the solvent was evaporated using vacuum rotary evaporator. The resulting residue was purified on silica gel column chromatography using n-hexane and ethyl acetate as eluent.

The synthetic route of 454-79-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Venu Saranya, Thachora; Rajan Sruthi, Pambingal; Anas, Saithalavi; Synthetic Communications; vol. 49; 2; (2019); p. 297 – 307;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 1003-98-1, 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. 1003-98-1, name is 2-Bromo-4-fluoroaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: m-CPBA(1.7 g, 8.0 mmol, 85%) was dissolved in 1,2-dichloroethane (15.0 mL) in a threeneckflask equipped with a condenser and heated to reflux (at rt in case of 1b).Then, the substrate aromatic amine (2.0 mmol) dissolved in 1,2-dichloroethane(5.0 mL) was added dropwise to the refluxing peracid solution. After 10 h, themixture was cooled to rt and quenched with saturated aqueous Na2S2O3. Thesolvent was removed under reduced pressure and the residue was treated with10% NaOH solution followed by extraction with EtOAc. The combined extracts were washed with H2O and brine, dried over anhydrous Na2SO4. Removal of thesolvent under vacuum afforded the crude product, which was purified bycolumn chromatography using hexane/ethyl acetate as eluant.

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-Bromo-4-fluoroaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Liu, Jia; Li, Jue; Ren, Jiangmeng; Zeng, Bu-Bing; Tetrahedron Letters; vol. 55; 9; (2014); p. 1581 – 1584;,
Bromide – Wikipedia,
bromide – Wiktionary

24358-62-1, name is 1-(4-Bromophenyl)ethylamine, 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. Product Details of 24358-62-1

Propionic anhydride (1.86g) was added to the solution of 1 -(4-bromophenyl)ethylamine (2.38g) and triethylamine (1.45g) in tetrahydrofuran (50ml), and the mixture was stirred at room temperature for 6 hours. The reaction mixture concentrated under reduced pressure, and the residue was purified by silica gel column chromatography to obtain N-[l-(4-bromophenyl)ethyl]propanamide (2.81g).1H-NMR (CDC13) delta: 1.15 (3H, t), 1.46 (3H, d), 2.21 (2H, q), 5.04-5.13 ( 1 H, m), 5.63 (1H, br s), 7.19-7.24 (2H, m), 7.44-7.47 (2H, m).

The synthetic route of 24358-62-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER CROPSCIENCE AG; MURATA, Tetsuya; HATAZAWA, Mamoru; BRUeCHNER, Peter; SHIMOJO, Eiichi; ICHIHARA, Teruyuki; ATAKA, Masashi; SHIBUYA, Katsuhiko; GOeRGENS, Ulrich; WO2011/51455; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

399-94-0, name is 1-Bromo-2,5-difluorobenzene, 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. category: bromides-buliding-blocks

Referential Example 34: 6-(t-Butyl-diphenylsilyloxy)-1-(2,5-difluorophenyl)-1-hexanol A tetrahydrofuran (30 ml) solution of 1-bromo-2,5-difluorobenzene (0.956 ml, 8.46 mmol) was stirred at -78C. To the reaction mixture was added a hexane solution (6.46 ml, 10.2 mmol) of n-butyl lithium.. The reaction mixture was added to a tetrahydrofuran (20 ml) solution of 6-(t-butyldiphenylsilyloxy)hexanal (2.50 g, 7.05 mmol) at -78C and the mixture was stirred at the same temperature for 30 minutes.. After the temperature of the reaction mixture was elevated to room temperature, diethyl ether was added thereto.. The mixture was washed with a saturated aqueous solution of ammonium chloride and the organic layer was dried over anhydrous sodium sulfate.. After filtration, the filtrate was concentrated under reduced pressure.. The residue was subjected to flash silica gel chromatography, and the fraction obtained from the hexane:ethyl acetate=9:1 elude was concentrated under reduced pressure, whereby the title compound (2.92 g, 4.65 mmol, 88%) was obtained as a colorless oil.1H-NMR (400MHz, CDCl3) delta: 1.04(9H,m), 1.21-1.90(8H,m), 3.64(2H,t,J=6.3Hz), 4.96(1H,t,J=6.5Hz), 6.86-7.01(2H,m), 7.13-7.20(1H,m), 7.32-7.45(6H,m), 7.62-7.70(4H,m).

The synthetic route of 399-94-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1466898; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 5433-01-2, These common heterocyclic compound, 5433-01-2, name is 1-Bromo-3-isopropylbenzene, 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 50 Preparation of Ethyl beta-Amino-m-Isopropylcinnamate. To the Grignard reagent prepared from 39.5 g (0.198 mol) of m-bromocumene and 4.9 g (0.20 mol) of magnesium in 150 ml of ether was added 11.2 g (0.099 mol) of ethyl cyanoacetate dropwise with stirring at 10. The mixture was stirred at reflux for 22 hours and was allowed to stand at 23 for four days. Then, 10.6 g (0.20 mol) of NH4 Cl in 60 ml of water was added with stirring at 10-15, followed by 0.20 mol of 2 N, HCl at 0. The layers were separated, and the water layer was extracted with 100 ml of ether. The ether layers were combined, extracted with dilute NaHCO3 solution, dried (CaSO4), and distilled to give 4.95 g of 80% pure product, boiling point 139-142 (0.15 torr) and 0.87 g of about 97% pure product, boiling point 142-143 (0.15 torr). [Infrared analysis of the lower-boiling impurity indicated it to be bi(m-cumenyl)]. Anal. Calc’d. for 97% C14 H19 NO2 -3% C18 H22: C, 72.60; H, 8.24; N, 5.82. Found: C, 72.60; H, 8.46; N, 5.84.

Statistics shows that 1-Bromo-3-isopropylbenzene is playing an increasingly important role. we look forward to future research findings about 5433-01-2.

Reference:
Patent; Monsanto Company; US4187099; (1980); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 2550-36-9, name is (Bromomethyl)cyclohexane, 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 2550-36-9, Recommanded Product: 2550-36-9

The compound prepared in Step 5 (35 mg, 0.08 mmol), (bromomethyl) cyclohexane (21 mg, 0.12 mmol), 2C03 (22 mg, 0.16 mmol), I (2 mg) in DMF (2 mL) was stirred at 90C for 16 hours under N2. The mixture was concentrated, diluted with DCM, washed with brine, dried over Na2S04, filtered and the solvent was evaporated. The residue was purified by prep-HPLC to give pure product (15 mg, yield: 35%).-NMR (400 MHz, CDC13) delta 7.97-7.93 (m, 2H), 7.73 (s, 1H), 7.58 (s, 1 H), 7.52-7.50 (m, 2H), 7.44-7.37 (m, 3H), 7.24-7.16 (m, 2H), 5.84 (s, 1H), 3.18-3.13 (m, 1 H), 2.99-2.97 (m, 4H), 2.95 (s, 3H), 1.74-1.58 (m, 1 H),1.54~1.51 (m, 2H), 1.43-1.41 (m, 2H), 1 .04-0.91 (m, 4H), 0.89-0.79 (m, 2H), 0.76-0.56 (m, 1H). MS (M+H)+: 535.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MCCOMAS, Casey, Cameron; LIVERTON, Nigel, J.; SOLL, Richard; LI, Peng; PENG, Xuanjia; WU, Hao; NARJES, Frank; HABERMANN, Joerg; KOCH, Uwe; LIU, Shilan; ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P. ANGELETTI, SRL; WO2011/106992; (2011); 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. 937046-98-5, name is 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine, A new synthetic method of this compound is introduced below., category: bromides-buliding-blocks

To a stirred suspension of 7-bromopyrrolo[2,1-f][1,2,4]triazin-4-amine (801 mg, 3.76 mmol), tert-butyl 4-[4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)phenyl]tetrahydro- 1 (2H)-pyrazinecarboxylate (2.19 g, 5.64 mmol), and [1 ,1′-bis(diphenylph?sphino)- ferrocene]dichloro palladium(ll)-complex with dichloromethane (275 mg, 0.38 mmol) in degassed DME (25 mL) was added aqueous Na2CO3 solution (2 M, 5.6 mL). The reaction was heated (80 0C) for 17 h and then cooled to rt. The mixture was filtered through a pad of Celite using ethyl acetate to rinse. The filtrate was washed with water (75 mL), dried (Na2SO4), and concentrated. The crude material was purified by ISCO chromatography using a gradient of 50 to 75% ethyl acetate in hexanes to afford 1.22 g (74%) of the desired product as an off-white solid, which contained trace impurities. 1H NMR (300 MHz, DMSO-de) delta 7.94-7.88 (m, 2 H), 7.86 (s, 1 H), 7.65 (br s, 2 H), 7.03-6.97 (m, 1 H), 6.94 (d, 1H), 6.89 (d, 1 H), 3.51-3.42 (m, 4 H), 3.19-3.11 (m, 4 H), 1.42 (s, 9 H); ES-MS m/z 395.1 [M+H]+, HPLC RT (min) 2.52.

The synthetic route of 937046-98-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2007/56170; (2007); A2;,
Bromide – Wikipedia,
bromide – Wiktionary