Month: July 2021

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

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,
bromide – Wiktionary

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

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. 24358-62-1, name is 1-(4-Bromophenyl)ethylamine, This compound has unique chemical properties. The synthetic route is as follows., name: 1-(4-Bromophenyl)ethylamine

EXAMPLE 141 N-[1-(4-bromophenyl)ethyl]-3-(biphenyl-2-carbonylamino)-benzoic acid amide Prepared analogously to Example 34 from 3-(biphenyl-2-carbonylamino)-benzoic acid, 1-(4-bromophenyl)ethylamine, TBTU and N-ethyldiisopropylamine in dimethylformamide. C28H23BrN2O2 (499.41) Mass spectrum:(M-H)-=497/499 (bromine isotopes)

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 24358-62-1.

Reference:
Patent; Priepke, Henning; Hauel, Norbert; Thomas, Leo; Mark, Michael; Dahmann, Georg; US2002/32238; (2002); 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., Recommanded Product: 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine

The bromopyrazole (prepared according to WO2009/132135) (0.5 g, 2.4 mmol) was suspended in anhydrous THF (10 mL) under N2(g). The suspension was stirred and TMSCl (0.67 mL, 5.28 mmol) was added. The mixture was stirred for 20 min. at RT and then cooled to -78 C. after which time a solution of n-BuLi (6 mL, 1.6 N in hexanes, 9.6 mmol) was added slowly. The reaction mixture was stirred for 10 min. at -78 C. and then the lactone (1 g, 2.4 mmol) was added via syringe. When the reaction was complete as measured by LCMS, AcOH was added to quench the reaction. The mixture was concentrated under reduced pressure and the residue dissolved in a mixture of CH2Cl2 and H2O (100 mL, 1:1). The organic layer was separated and washed with H2O (50 mL). The organic layer was then dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The residue was subjected to silica gel chromatography eluting with 0-50% EtOAc in hexanes to provide the product as a 1:1 mixture of anomers (345 mg, 26% yield). LCMS m/z 553 [M+H].

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; Gilead Sciences, Inc.; Clarke, Michael O’ Neil Hanrahan; Feng, Joy Yang; Jordan, Robert; Mackman, Richard L.; Ray, Adrian S.; Siegel, Dustin; (116 pag.)US2017/71964; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 7745-91-7,Some common heterocyclic compound, 7745-91-7, name is 3-Bromo-4-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.

General procedure: The substituted amines (2mmol) and triethylamine were taken in THF (20mL) and anhydrous potassium carbonate was added (600mg) to it. A solution of 3 (2mmol), in THF (10mL) was added drop wise with stirring for 30min. The reaction mixture was refluxed for 10h. After completion of the reaction (TLC), the reaction mixture was then desolventized in rotavapor and the compound is extracted in dichloromethane. The dichloromethane layer was washed with water and dried over anhydrous Na2SO4 and further desolventization in rotary evaporator to get the desired compound. Structure verification data for novel compounds are documented in Supplementary File.

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-4-methylaniline, its application will become more common.

Reference:
Article; Prashanth; Madaiah; Revanasiddappa; Veeresh; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; vol. 110; (2013); p. 324 – 332;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 452-63-1,Some common heterocyclic compound, 452-63-1, name is 1-Bromo-4-fluoro-2-methylbenzene, 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.

A mixture of 2-bromo-5fluorotoluene (3.5 g, 18.5 mmol) and CuCN (2 g, 22 mmol) in DMF (100 mL) was refluxed for 24 hours. The reaction was diluted with water and extracted with hexane. The organics were dried over MgSO4 and the solvent removed to give product 31 (yield 60%). 1H-NMR (400 MHz, CDCl3): delta 7.60 (dd, J=5.6, 8.8 Hz, 1H), 6.93-7.06 (m, 2H), 2.55 (s, 3H).

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

Reference:
Patent; Takeda San Diego, Inc.; EP1586571; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

2862-39-7, name is 2-Bromo-N,N-dimethylethanamine hydrobromide, 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. COA of Formula: C4H11Br2N

The product (60mg, 0.17mmol) in 127 cases of [0479] embodiment taken dissolved in N, N- dimethylformamide (DMF, IOmL) was added cesium carbonate (125mg, 0.38mmol) and N, N- dimethyl amine bromoethane hydrobromide (45mg, 0.19mmol), 50 C oil bath and the reaction overnight, TLC detection, the reaction was complete, water chestnut evaporated to dryness and dissolved. (/=15:1)-1 (3 (2-(-5 (34–2-49mg70%) Column chromatography (dichloromethane / methanol = 15: 1) to give the product -1 (3 (2- (dimethylamino) ethoxy) benzyl) -5- (3,4-dimethoxybenzyl) pyrrolidin-2-one (49mg, 70%).

The synthetic route of 2862-39-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Hu Youhong; Leng Ying; Duan Shudong; Huang Suling; (120 pag.)CN103626713; (2017); B;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 102169-44-8, A common heterocyclic compound, 102169-44-8, name is 4-Bromo-5-methylbenzene-1,2-diamine, molecular formula is C7H9BrN2, 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.

4-bromo-5-methylbenzene-1,2-diamine (0.5 g, 2.3 mmol) and cyclopropanecarboxaldehyde (207 mg, 18 mmol) was dissolved in 7.5 ml of ethanol and cobalthydroxide (22 mg, 0.24 mmol) blended. The reaction mixture was stirred overnight, opened the lid, filtered and concentrated under reduced pressure to dryness. The residue was By chromatography were purified (2chiLabomatic HD-3000 spring via HPLC, Labomatic AS-3000> Knauer DAD 2600 5 Labomatic Labcol Vario 4000 Plus Chromatorex C18 10 micron 125 mm chi 30 mm +250 mm chi 50.8 mm; eluent A: water volume +0.2 /. Ammonia (32%), Eluent B: methanol, gradient: 0-12 min 70-100% B; flow rate: 100 ml / min). 184 mg (31% of the theoretical value) of this compound to produce the subject.

The synthetic route of 102169-44-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; ROEHN, ULRIKE; ELLERMANN, MANUEL; STRASSBURGER, JULIA; WENDT, ASTRID; ROEHRIG, SUSANNE; WEBSTER, ROBERTALAN; SCHMIDT, MARTINAVICTORIA; TERSTEEGEN, ADRIAN; BEYER, KRISTIN; SCHAEFER, MARTINA; BUCHMUELLER, ANJA; GERDES, CHRISTOPH; SPERZEL, MICHAEL; SANDMANN, STEFFEN; HEITMEIER, STEFAN; HILLISCH, ALEXANDER; ACKERSTAFF, JENS; TERJUNG, CARSTEN; (148 pag.)TW2016/5809; (2016); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 2576-47-8,Some common heterocyclic compound, 2576-47-8, name is 2-Bromoethylamine hydrobromide, molecular formula is C2H7Br2N, 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.

2-Bromoethylamine hydrobromide (500 mg, 2.44 mmol) and sodium azide (475.9 mg, 7.32 mmol) were dissolved in water (2 mL). The solution was heated to 75 C, stirred for 21 h, cooled to 0 C, Potassium (800 mg) and diethyl ether (2 mL). Purified by chloroform-methanol (20:1) column chromatography2-azidoethylamine (171 mg, 82%).

The synthetic route of 2576-47-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; China Institute Of Forestry Forest Products Chemical Industry Institute; Nanjing Zhongsen Biological Technology Co., Ltd.; Wang Chengzhang; Qi Zhiwen; (7 pag.)CN109180594; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary