Tag: M.W=200-300

These common heterocyclic compound, 314084-61-2, name is 2-Bromo-1,3-diethyl-5-methylbenzene, 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. Formula: C11H15Br

Under a nitrogen atmosphere, 13.9 G of malonic acid dinitrile are added at normal pressure and room temperature to 20.4 g of pulverulent sodium hydroxide in 240 g of 1-methyl-2- pyrrolidone. After the addition of 45.5 g of 2-bromo-1, 3-diethyl-5-methylbenzene, the reaction mixture is heated to 125C with stirring. At that temperature, a mixture of 1.3 g of triphenylphosphine, 1.06 g of a commercially AVAILABLE PALLADIUM (II) chloride solution in concentrated hydrochloric acid (20% Pd content corresponding to 0.354 g of Pd (LI) chloride and 0.708 g of concentrated hydrochloric acid) and 97.6 g of 1-methyl-2-pyrrolidone is added. Stirring is carried out for a further 3 hours at from 125 to 130C, and 283 g of diluent are distilled off at reduced pressure (from 17 to 100 mbar). After cooling to room temp- erature, the reaction mixture is added to 70 g of water. Following the addition of 38 g of concentrated hydrochloric acid (a pH value of less than 5 is then established), the precipitated solid is filtered off and washed with 60 g of water. After drying, 42.4 G of 2- (2, 6- diethyl-4-methylphenyl) malonic acid dinitrile (content 92.3%, yield 92.3%) having a melting point of from 74 to 78C are obtained.Example P4: Preparation of 2- (2, 6-diethyl-4-methylphenyl) malonic acid dinitrile Under a nitrogen atmosphere and at normal pressure, 14 g (217 MMOL) of malonic acid dinitrile dissolved in 7 ml of 1-methyl-2-pyrrolidone are added dropwise in the course of 30 minutes, at from 20 to 25C, to a mechanically stirred mixture of 24.1 g (600 MMOL) of sodium hydroxide (pellets) in 300 ml of 1-methyl-2-pyrrolidone. Evacuation to from 10 to 30 mbar is carried out and, at from 80 to 100C, 113 g of solvent are distilled off. After establishing normal pressure, 48 g (content 94.9% ; 200 MMOL) of 2-bromo-1, 3-DIETHYL-5- METHYLBENZENE are added and the reaction mixture is heated to 130C. At that temperature, a mixture of 0.26 g (1 MMOL) of triphenylphosphine, 0.21 g of a commercially available palladium (li) chloride solution in concentrated hydrochloric acid (20% Pd content corresponding to 0.071 g (400 UMOL) of PALLADIUM (II) CHLORIDE in 0.142 g of concentrated hydrochloric acid) and 19.5 g of 1-methyl-2-pyrrolidone is added. The reaction mixture is stirred for from 2 to 3 hours at from 125 to 140C, nitrogen being introduced below the surface. A further 165 g of solvent are distilled off at from 20 to 60 mbar. 2.3 g of Hyflo and 150 ml of water are added to the residue which has been cooled to 50C. The reaction mixture is stirred vigorously for 10 minutes and then clarified by filtration over Hyflo. The filter is subsequently washed with 55 ml of water. The combined aqueous phases are extracted once with 91 g of toluene. The organic phase is separated off and discarded. 30 g of toluene/water are distilled off from the aqueous phase at from 20 to 70C and from 200 to 250 mbar. At from 20 to 25C there are added to the distillation sump, in the course of from 60 to 80 minutes, 45.7 g of 32% hydrochloric acid, during the course of which the product crystallises out and the pH value falls to from 4.0 to 4.5. Filtration with suction is carried out, followed by washing with 120 ml of water (divided into 2 portions). The product is dried in a vacuum drying cabinet for 16 hours at from 100 to 250 mbar. 42.2 g (content 98.2% ; yield 97.6%) of 2- (2, 6-DIETHYL-4-METHYLPHENYL) MALONIC acid dinitrile are obtained.

The synthetic route of 2-Bromo-1,3-diethyl-5-methylbenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; WO2004/50607; (2004); A1;,
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Synthetic Route of 327-51-5, A common heterocyclic compound, 327-51-5, name is 1,4-Dibromo-2,5-difluorobenzene, molecular formula is C6H2Br2F2, 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.

(1380) [00444] Into a 50-mL round-bottom flask that was purged and maintained under an inert atmosphere of nitrogen was added 1 ,4-dibromo-2,5-difiuorobenzene (1.50 g, 5.52 mmol), tert- butyl 4-(tetramethyl-l,3,2-dioxaborolan-2-yl)-l,2,3,6-tetrahydropyridine-l-carboxylate (1.88 g, 6.06 mmol), potassium carbonate (2.28 g, 16.5 mmol), Pd(dppf)Cb’CH2Cl2 (400 mg, 0.49 mmol), DMF (20 mL) and H2O (2 mL). The reaction mixture was stirred for 2 h at 50 C and then cooled and quenched with water (20 mL). The resulting solution was extracted with ethyl acetate (3 x 50 mL). The combined organic layers were washed with water (50 mL) and brine (50 mL). The organic layer was then concentrated in vacuo. The resulting crude product was purified by FCC eiuting with petroleum ether/ethyl acetate (5: 1) to afford fer/-butyl 4-(4-bromo- 2,5-difluorophenyl)-3,6-dihydropyridine-l(2 )-carboxylate (1.5 g, 73%). H-NMR (300 M ( DO delta ppm 7.21-7.29 (m, 1H), 6.93-7.08 (m, 1H), 5.81-5.61 (m, 1H), 4.01-4.14 (m, 2H), 3.62 (t, J – 5,7 Hz, 2H), 2.48-2.51 (m, 2H), 1 ,50 (s, 9H).

The synthetic route of 327-51-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FORMA THERAPEUTICS, INC.; GUERIN, David Joseph; BAIR, Kenneth W.; CARAVELLA, Justin A.; IOANNIDIS, Stephanos; LANCIA JR., David R.; LI, Hongbin; MISCHKE, Steven; NG, Pui Yee; RICHARD, David; SCHILLER, Shawn E. R.; SHELEKHIN, Tatiana; WANG, Zhongguo; (365 pag.)WO2017/139778; (2017); A1;,
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Reference of 627871-16-3, These common heterocyclic compound, 627871-16-3, name is 5-Bromo-4-fluoro-2-methylaniline, 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.

In a 250 mL round-bottomed flask was placed 4-(pyridin-2-ylmethoxy)benzoic acid (3.4 g, 14.7) in DCM (50 mL) to give a suspension. To the solution, SOCl2 (22.29 mL, 305.37 mmol) was added. The mixture was stirred at RT overnight. Concentration removed SOCl2 and DCM to give crude 4-(pyridin-2-ylmethoxy)benzoyl chloride. To the residue was added 5-bromo-4-fluoro-2-methylaniline (3.0 g, 14.70 mmol), DIPEA (6.42 mL, 36.76 mmol), and DCM (60 mL) to give a black solution. The reaction was stirred at RT overnight. Concentration under reduced pressure gave the crude product, which was purified by ISCOMPLC (0-6% MeOH/DCM) to give the title compound.

Statistics shows that 5-Bromo-4-fluoro-2-methylaniline is playing an increasingly important role. we look forward to future research findings about 627871-16-3.

Reference:
Article; Bodnarchuk, Michael S.; Brassil, Patrick; Dakin, Les; Daly, Kevin; Godin, Robert; Hattersley, Maureen M.; Hird, Alexander W.; Janetka, James W.; John Russell, Daniel; Redmond, Sean; Su, Qibin; Yang, Bin; Zheng, Xiaolan; Bioorganic and medicinal chemistry; vol. 28; 2; (2020);,
Bromide – Wikipedia,
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Reference of 6627-78-7,Some common heterocyclic compound, 6627-78-7, name is 1-Bromo-4-methylnaphthalene, molecular formula is C11H9Br, 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 1-bromo-4-methylnaphthalene (1.0 g, 4.52 mmol, 1.0 eq), tert-butyl 4- (4,4,5, 5-tetramethyl-l,3,2-dioxaborolan-2-yl)-3,6-dihydropyridine-l(2H)-carboxylate (2.1 g, 6.78 mmol, 1.5 eq) and Na2C03 (1.43 g, 13.56 mmol, 3.0 eq) in a mixture of 1,2-DME (15 mL) and water (5 mL) was purged with nitrogen for 15 min. Pd(dppf)Cl2 DCM (0.36 g, 0.45 mmol, 0.1 eq) was added to the reaction mixture and was stirred under nitrogen atmosphere, at 80 C for 2 h. After complete consumption of starting material, the mixture was cooled to ambient temperature and partitioned between water and ethyl acetate. The organic extract was separated and the aqueous extract was again extracted with ethyl acetate. The combined organic extract was washed with brine, dried over anhydrous Na2S04, filtered and solvents evaporated from the filtrate under reduced pressure to obtain a crude product, which was purified by flash chromatography on silica gel, 230-400 mesh, using gradient of ethyl acetate in hexanes as eluent to obtain tert-butyl 4-(4-methylnaphthalen-l-yl)-3,6-dihydropyridine-l(2H)-carboxylate. LCMS: Purity 82.42%. MS calculated for [M]323.44 and found [M+H] +324.20

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-methylnaphthalene, its application will become more common.

Reference:
Patent; PORTOLA PHARMACEUTICALS, INC.; PANDEY, Anjali; BOWERS, Simeon; BARTA, Thomas E.; BOURNE, Jonathan William; (208 pag.)WO2017/147328; (2017); A1;,
Bromide – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 1435-51-4, name is 1,3-Dibromo-5-fluorobenzene, 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 1435-51-4, category: bromides-buliding-blocks

A solution of l,3-dibromo-5-fluorobenzene (0.50 g, 1.99 mmol), 3-thiopheneboronic acid (0.254 g, 1.99 mmol), 2.0 M aqueous Sodium carbonate (1.99 niL, 3.97 mmol) and Pd(PPh3)4 (115 mg, 0.10 mmol) in toluene (9.2 mL) and ethanol (2.4 mL), was heated at 1000C for 1.5 hours by microwave. The product mixture was diluted with EtOAc (100 mL) filtered, washed with water (50 mL), brine (50 mL), dried with Na2SO4 and concentrated. Flash chromatography (2% EtOAc in hexane, silica) resulted in 400 mg of pure product as a clear oil.

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; ARENA PHARMACEUTICALS, INC.; WO2006/65600; (2006); A2;,
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Synthetic Route of 1435-51-4, 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. 1435-51-4, name is 1,3-Dibromo-5-fluorobenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 1,3-dibromo-5-fluorobenzene (LXI) (2.0 g, 7.88 mmol) in toluene (20 ml) was added potassium t-butoxide (2.65 g, 23 6 mmol) and 1-methylpiperazine (1.75 mL, 15.8 mmol). The reaction was heated at 105 C. overnight. The toluene was removed under vacuum and the residue was dissolved in water and extracted with EtOAc. The organic phase was separated, washed with brine, dried over MgSO4 and concentrated to dryness. The crude product was purified on a silica gel column (1:99 MeOH:CHCl3?7:93 MeOH:CHCl3) to produce 1-(3-bromo-5-fluorophenyl)-4-methylpiperazine (LXII) as an orange oil (800 mg, 2.93 mmol, 37.2% yield). 1H NMR (DMSO-d6, 500 MHz) delta ppm 2.20 (s, 3H), 2.39 (t, J=5 Hz, 4H), 3.33 (t, J=5 Hz, 4H), 6.74-6.81 (m, 2H), 6.91 (s, 1H); ESIMS found for C11H14BrFN2 m/z 273 (M+H).

The synthetic route of 1,3-Dibromo-5-fluorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Samumed, LLC; Hood, John; Kumar KC, Sunil; Wallace, David Mark; US2013/296302; (2013); A1;,
Bromide – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 5003-71-4, name is 3-Bromopropan-1-amine hydrobromide, 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 5003-71-4, Product Details of 5003-71-4

In a solution of 3-bromopropan-1 -amine hydrobromide (1.00 g, 0.46 mmol) in THE (40m1) trimethylamine (imI, 0.58 mmol) is added and the resulting reaction mixture isstirred for half an hour, then catalytic amount of 2-methylaminopyridine is added into the reaction mixture. Einally, in ice cold condition 1.23 ml of Boc anhydride is also added into it, in a dropwise manner and the reaction mixture is stirred for overnight. Now slowly, the reaction mixture is quenched with ammonium chloride and extracted with ethyl acetate. The combined organic phase is washed with brine and finally dried over anhydrousNa2504. The crude product is further purified by flash chromatography by using 60-1 20mesh silica gel and ethyl acetate/hexane as mobile phase. The product tert-butyl (3-bromopropyl)carbamate is obtained as a yellowish solid upon cooling at 4 00 (Yield: 0.9 g(83%))

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Bromopropan-1-amine hydrobromide, and friends who are interested can also refer to it.

Reference:
Patent; SHIV NADAR UNIVERSITY; ROY, Gouriprasanna; BANERJEE, Mainak; KARRI, Ramesh; CHALANA, Ashish; DAS, Ranajit; (61 pag.)WO2017/168451; (2017); A1;,
Bromide – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 1198171-18-4, name is 1-Bromo-2-(difluoromethyl)-4-fluorobenzene, 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 1198171-18-4, Recommanded Product: 1198171-18-4

Step 2) Preparation of2-(difluoromethyl)-4-fluorobenzaldehyde (78): Isopropyl magnesium bromide (30 mL,l M in THF, 30 mmol) was added dropwise to an ice-cooled solution of l-bromo-2-(difluoromethyl)-4-fluorobenzene (77; 6g,26.7mmol) in THF (100 mL). The reaction mixture was then allowed to warm to room temperature and stirred for 3 hr. Dimethylformamide (3.5 mL, 45.2 mmol) was added and the reaction stirred for 3 hr. Water was added and the mixture was extracted with ethyl acetate. The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure. The resulting residue was purified by chromatography to afford 2- (difluoromethyl)-4-fluorobenzaldehyde 78 (3.2g, 68%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-2-(difluoromethyl)-4-fluorobenzene, and friends who are interested can also refer to it.

Reference:
Patent; SIRTRIS PHARMACEUTICALS, INC.; WO2009/146358; (2009); A1;,
Bromide – Wikipedia,
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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. 103273-01-4, name is 2-Bromo-4-(tert-butyl)aniline, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Bromo-4-(tert-butyl)aniline

2-Bromo-4-tert-butyl-phenylamine (162 g, 0.71 mol) was added dropwise to H2SO4 (410 mL) at room temperature to yield a clear solution. This clear solution was then cooled down to -5 to -10 C. A solution of KNO3 (82.5 g, 0.82 mol) in H2SO4 (410 mL) was added dropwise while the temperature was maintained between -5 to -10 C. Upon completion, the reaction mixture was poured into ice/water and extracted with EtOAc. The combined organic layers were washed with 5% Na2CO3 and brine, dried over Na2SO4 and concentrated. The residue was purified by a column chromatography (EtOAc/petroleum ether 1/10) to give 2-bromo-4-tert-butyl-5-nitro-phenylamine as a yellow solid (152 g, 78%).

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; Vertex Pharmaceuticals Incorporated; US2012/309758; (2012); A1;,
Bromide – Wikipedia,
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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. 49764-63-8, name is 4,5-Dibromobenzene-1,2-diamine, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C6H6Br2N2

To a solution of methyl (S)-4-(2-(2-formylbenzoyl)-5,5,8a-trimethyl-1,2,3,5,8,8a- hexahydroisoquinolin-6-yl)benzoate (50 mg, 0.113 mmol) and 4,5-dibromobenzene-1,2- diamine (30 mg, 0.113 mmol) in DMF (2 ml) was added sodium metabisulfite (24 mg, 0.124 mmol). The mixture was stirred at 60 C overnight. The mixture was concentrated in vacuo. The residue was partitioned between EtOAc (20 ml) and H2O (20 ml). The separated aqueous layer was extracted with EtOAc (20 ml). The combined organic layers were washed brine (20 ml), dried over Na2S04, and concentrated in vacuo. The crude product was purified by silica gel column eluted with 35 % EtOAc / hexanes to give the desired product (62 mg, 80 %) as a solid. LC/MS m/z 688.10 (M+H)+, 2.91 min (Method 2).

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 49764-63-8.

Reference:
Patent; VIIV HEALTHCARE UK (NO.5) LIMITED; CHEN, Jie; MEANWELL, Nicholas A.; REGUEIRO-REN, Alicia; SIT, Sing-Yuen; SWIDORSKI, Jacob; (267 pag.)WO2018/2848; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary