Month: July 2021

Application of 67567-26-4, A common heterocyclic compound, 67567-26-4, name is 4-Bromo-2,6-difluoroaniline, molecular formula is C6H4BrF2N, 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-2,6-difluoroaniline (5.00 g, 24.0 mmol, 1.00 equiv) and copper(I) cyanide (6.45 g, 72.0 mmol, 3.00 equiv) were suspended in 50 mL DMF and heated at 120 C for 24 h. After cooling to room temperature, the mixture was poured into an aqueous solution of ammonia (12%, v%, 250 mL). The mixture was then filtered and the precipitate was washed with EtOAc (500 mL). The organic phases were combined and washed with the ammonia solution (500 mL), distilled water (500 mL), brine (500 mL) and dried over anhydrous MgSO4. Solvents were removed under reduced pressure. The crude was purified by flash column chromatography (CH2Cl2/n-pentane, 2:1, v/v) to yield the desired compound (1.88 g, 12.2 mmol, 51%) as a white solid.

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; Zhang, Lei; Linden, Greta; Vazquez, Olalla; Beilstein Journal of Organic Chemistry; vol. 15; (2019); p. 2500 – 2508;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 626-40-4, name is 3,5-Dibromoaniline, 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 626-40-4, Quality Control of 3,5-Dibromoaniline

The 5.018 (0.02 muM) 3, 5 – dibromoaniline and 7.149 g (0.05 muM) (5 – aminothiophen – 2 – yl) boronic acid is added to a 500 ml three-neck bottle in, adding 400 ml tetrahydrofuran (THF), then adding 2 mol/L potassium carbonate solution of 75 ml, and add 0.5 ml of aliquat 336, magnetic stirring and open the argon gas, oil bath is heated to 75 C after, adding 0.020 g […] palladium, reflux reaction 24 h, the reaction liquid is poured into the water in the, a large amount of precipitate out. For funnel, evaporating the solvent under reduced pressure. The product in order to dichloromethane: hexane=3:1 ([…]) as the mobile phase silica gel as stationary phase makes the column chromatographic purification, collecting products and turns on lathe does, in 90 C drying in vacuum 24 h, to obtain the target product 4.311 g, yield is 75%.

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, 3,5-Dibromoaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hunan University of Technology; Ding Qian; Tan Jinghua; Liu Yiwu; Fu Hao; (20 pag.)CN109053466; (2018); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 766-46-1, 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. 766-46-1 name is 2′-Bromophenylacetylene, 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.

General procedure: All homocoupling reactions of aromatic terminal alkyneswere carried out under air. A mixture of aromatic terminal alkyne (1.0 mmol), NEt3 (1.0 mmol) and P-O coordinatedcyclopalladated complex 1 (0.005 mmol)/AgNO3 (0.5 mmol) inTHF:H2O (in 4:1 proportion, 2.5 mL) was allowed to react at60C. The reaction progress was analyzed by GLC. The mixturewas added brine (4 mL) and extracted three times with ethylacetate (3 × 15 mL), dried over Na2SO4, concentrated in vacuoand purifed by thin layer chromatography. The purifed products were identifed by 1H-NMR and 13C-NMR spectroscopy.The Supplemental Materials presents sample 1H and 13C NMRspectra of the diyne products (Figures S1-S24).

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

Reference:
Article; Chen, Bo; Guo, Mengping; Wen, Yongju; Shen, Xiuli; Zhou, Xiuling; Lv, Meiyun; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 192; 3; (2017); p. 259 – 263;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 51776-71-7, name is 1-Bromo-4-(difluoromethyl)benzene, molecular formula is C7H5BrF2, 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. category: bromides-buliding-blocks

Example 33A 1-Bromo-4-[bromo(difluoro)methyl]benzene With exclusion of oxygen, a solution of 14.0 g (67.63 mmol) of 1-bromo-4-(difluoromethyl)benzene [CAS 51776-71-7] and 25.3 g (142 mmol) of N-bromosuccinimide (NBS) in 190 ml of tetrachloromethane is irradiated with a sun lamp. During this, the solvent reaches its boiling point. It is irradiated under reflux for 24 hours. The mixture is then allowed to cool to room temperature and precipitated succinimide is filtered off. The filtrate is again mixed with 25 g of NBS and irradiated once more with exclusion of oxygen under reflux for 24 hours. Cooling is followed by filtration again, and the filtrate is concentrated to dryness. 18 g of an orange-colored oil are obtained as crude product, which is purified further by vacuum distillation at 13 mmHg. 12.7 g (44.4 mmol, 66% yield) of a colorless oil are obtained. Boiling point (13 mmHg): 90-92 C. 1H-NMR (300 MHz, DMSO-d6, o/ppm): 7.79 (2H, d), 7.63 (2H, d). MS (ESI): 205/207 (M-Br+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 51776-71-7, its application will become more common.

Reference:
Patent; BAYER HEALTHCARE AG; US2009/227640; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 656-64-4,Some common heterocyclic compound, 656-64-4, name is 3-Bromo-4-fluoroaniline, molecular formula is C6H5BrFN, 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 206 4-(3-Bromo-4-fluoro-phenylamino)-7-methoxy-6-nitro-quinoline-3-carbonitrile A mixture of 3.52 g (9.7 mmol) of 4-chloro-7-methoxy-6-nitro-3-quinolinecarbonitrile and 2.0 g (10.7 mmol) of 3-bromo-4-fluoro aniline in 150 ml of methoxyethanol was refluxed under nitrogen for 5.5 hours. The reaction mixture was diluted with ethyl acetate and wash with sodium bicarbonate solution and sodium chloride solution. The organic layer was dried with sodium sulfate and then solvent was removed under vacuum. The residue was chromatographed on silica gel eluding with mixture of ethyl acetate and methanol to give 3 g of yellow solid: mass spectrum (electrospray, m/e): 416.8 and 418.8.

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-fluoroaniline, its application will become more common.

Reference:
Patent; American Cyanamid Company; US6384051; (2002); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 1003-99-2, These common heterocyclic compound, 1003-99-2, name is 2-Bromo-5-fluoroaniline, 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.

The N-(t-butyloxycarbonyl)-4-piperidone (10.13 g, 50.8 mmol, 1.0 eq) and the 2-bromo-5-fluoroaniline (11.6Og, 61.0 mmol, 1.2 eq.) were weighed into a flask. Acetic acid (75 mL) was added, followed by trimethylsilyl cyanide (7.75 mL, 58.1 mmol, 1.14 eq.). The mixture was stirred at rt for 24 hr, and was then added to a mixture of 200 mL ice and 200 mL saturated ammonium hydroxide solution. The resulting mixture was extracted twice with methylene chloride, and the organic solution was dried over magnesium sulfate, filtered, and concentrated to provide 22.57g of crude product.

Statistics shows that 2-Bromo-5-fluoroaniline is playing an increasingly important role. we look forward to future research findings about 1003-99-2.

Reference:
Patent; MERCK & CO., INC.; SUNESIS PHARMACEUTICALS, INC.; WO2006/44497; (2006); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 2924-09-6, 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. 2924-09-6, name is 5-Bromo-2-fluoroaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

In an argon atmosphere, 106 mL of water was added to 10g of 5-bromo-2-fluoroaniline, and the mixture wasstirred, followed by addition of 79.2 mL of concentrated hydrochloric acid. The resulting mixture was cooled in ice, andan aqueous solution of 4.36g of sodium nitrate was added dropwise. While cooling in ice, the resultant was stirred for30 minutes, and then an aqueous solution of 87.3g of potassium iodide was added. After extraction with ethyl acetate,an organic layer was washed with an aqueous solution of a saturated sodium hydrogen carbonate and an aqueoussolution of sodium sulfite and dried with magnesium sulfate. Then, the solvent was distilled off under reduced pressure.Residues were purified by silica gel column chromatography, whereby 11.5g (yield: 73%) of 5-bromo-2-fluoroiodebenzenewas obtained.

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, 5-Bromo-2-fluoroaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Idemitsu Kosan Co., Ltd; ITO, Hirokatsu; SAITO, Hiroyuki; MIZUKI, Yumiko; KAWAMURA, Masahiro; EP2924029; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 454-79-5, name is 2-Bromo-5-(trifluoromethyl)aniline, 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 454-79-5, category: bromides-buliding-blocks

70% Sulfuric acid (18 mL) was added drop-wise to the solution of 2-bromo-5- (trifluoromethyl)aniline (5.0 g, 21.0 mmol, 1.0 eq), propane- 1, 2,3 -triol (3.8 g, 42.0 mmol, 2.0 eq) and sodium m-Nitrobenzene sulfonate (7.3 g, 32.55 mmol, 1.55 eq) at 0 C and the mixture was stirred under nitrogen atmosphere, at 150 C for 4 h. After complete consumption of starting material, the mixture was cooled to ambient temperature, poured into chilled water and filtered through a celite bed. The filtrate was neutralized with 2N aqueous NaOH, which led to a precipitate, which was filtered and dried under vacuum to obtain 8-bromo-5- (trifluoromethyl)quinoline. LCMS: Purity 95.13%. MS calculated for [M] 274.96 and found [M+H] +276.04.

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-5-(trifluoromethyl)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PORTOLA PHARMACEUTICALS, INC.; PANDEY, Anjali; BOWERS, Simeon; BARTA, Thomas E.; BOURNE, Jonathan William; (208 pag.)WO2017/147328; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 955959-84-9, 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. 955959-84-9, name is 4-(4-Bromophenyl)dibenzo[b,d]furan belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

In an argon atmosphere, in a three-necked 100mL flask, compound (x) 0.8g, the compound (xi) 0.54g, bis(dibenzylideneacetone)palladium (0) (Pd(dba)2) 0.06g, tri-t-butylphosphine ((t-Bu)3P) 0.12g, was added to sodium t-butoxide 0.3g, was heated under reflux for 7 hours in 30mL of toluene solvent. After air-cooling, water was added The organic layer was separated, and the solvent was distilled off. The crude product thus obtained was purified by silica gel column chromatography (dichloro methane and using a mixed solvent of hexane) was subjected to recrystallization with toluene and hexane mixture solvent to give the compound A-35 as a white solid 0.95g (80percent yield)

The synthetic route of 4-(4-Bromophenyl)dibenzo[b,d]furan has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Samsung DisplayCo., Ltd.; Huchiwaki, Junta; Oyama, Hiromi; Miyata, Yasuo; Sakamoto, Naoya; Ueno, Masatsuku; Takada, Echinori; (155 pag.)KR2015/90021; (2015); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 59907-13-0, These common heterocyclic compound, 59907-13-0, name is 2-Bromo-1-fluoro-3-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.

To a solution of 2-bromo-l-fluoro-3-methylbenzene (2.5 g, 10 mmol) in THF (20 mL) at -70 C was added n-BuLi (1.6 M in hexane) (6.9 mL, l l .Ommol) dropwise over 5 min by syringe along the wall of the flask. After adding, the reaction was stirred at this temperature for 30 min. Then the resulting solution was added into a solution of (S)- tert-butyl l,6-dioxohexahydropyrrolo[l,2-a]pyrazine-2(lH)-carboxylate (2.07 g, 11.0 mmol) in THF (10 mL). After stirred at -70C for 5 min, the reaction mixture was quenched with saturated NH4CI and extracted with EtOAc (2 x 20 mL), washed with brine, dried over Na2S04, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography to give the title compound (2.2 g, yield : 40%); m/z (ES+) : 365 [M + H] + .

Statistics shows that 2-Bromo-1-fluoro-3-methylbenzene is playing an increasingly important role. we look forward to future research findings about 59907-13-0.

Reference:
Patent; LEO PHARMA A/S; BLADH, Haakon; FELDING, Jakob; ZHOU, Ding; CAI, Zhen-wei; SØRENSEN, Morten Dahl; WO2015/24878; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary