Month: February 2021

Synthetic Route of 38573-88-5, 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. 38573-88-5, name is 1-Bromo-2,3-difluorobenzene, This compound has unique chemical properties. The synthetic route is as follows.

Under nitrogen atmosphere, diisopropylamine (5.8 g) was dissolved in THF (30 mL) and cooled to -70 ¡ã C. or lower. To the solution, a 1.6 M butyllithium / hexane solution (32 mL) was added dropwise at such a rate that the inner temperature did not reach -65 ¡ã C., and the mixture was subsequently stirred at -70 ¡ã C. or lower for 30 minutes.Subsequently, a solution prepared by dissolving 2,3-difluorobromobenzene (10 g) in THF (50 mL) was added dropwise to the stirring reaction solution at a rate such that the internal temperature did not exceed -65 ¡ã C.,The mixture was stirred at -70 ¡ã C. or lower for 1 hour to prepare phenyllithiums.In a separate reaction vessel, a solution of difluorodibromomethane (16.3 g) dissolved in THF (160 mL) was cooled to -70 ¡ã C. or lower, and a solution of the phenyllithium prepared in advance was added to the solution in a cannula , Followed by stirring at -70 ¡ã C. or lower for 1 hour,And the mixture was heated to room temperature.Water and hexane were added to the reaction solution to separate the organic layer, and the organic layer was washed twice with saturated brine.Sodium sulfate was added to the organic layer after washing, dried, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 4-bromo-2,3-difluoro- (bromodifluoromethyl) benzene and 1,4 – dibromo-2,3-difluorobenzene (14.5 g). By measuring the ratio of each compound in the mixture using gas chromatography, 78.5percent of 4-bromo-2,3-difluoro- (bromodifluoromethyl) benzene, 1,4-dibromo- 3-Difluorobenzene was 21.5percent.

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-2,3-difluorobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; DIC CORPORATION; TOJO, KENTA; KUSUMOTO, TETSUO; TAKATSU, HARUYOSHI; (13 pag.)JP6019595; (2016); B2;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 156682-52-9,Some common heterocyclic compound, 156682-52-9, name is 1,4-Dibromo-2,3-difluorobenzene, molecular formula is C6H2Br2F2, 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.

Preparation of tert-butyl 3-[4-Bromo-3-(3-chloro-5-cyano-phenoxy)-2-fluoro-phenyl]-propionate (Step Numbers Refer to Scheme B)step 1-To a solution 3-chloro-5-hydroxy-benzonitrile (153 mg, 1 mmol) and DMA (1 muL) was added NaH (42 mg, 1.05 equiv., 60% mineral oil dispersion) and the resulting mixture was stirred at 50 C. for 30 min. To the solution was added B-1 (2.7 g, 10 mmol) and the resulting mixture was heated at 125 C. for 2 h. The solution was cooled and diluted with EtOAc and the resulting solution washed with an equal volume of 10% H2SO4. The organic extract was dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with 10% EtOAc/hexane to afford 331 mg (82%) of B-2a (Ar=3-chloro-5-cyano-phenyl).

The synthetic route of 156682-52-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Roche Palo Alto LLC; US2008/293664; (2008); 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 393-36-2 as follows. Formula: C7H5BrF3N

3-[4-bromo-3-(trifluoromethyl)phenyl[[3-(trifluoromethyl)phenyl]methyl]amino]-1,1,1-trifluoro-2-propanol EX-625A) The alpha,alpha,alpha-trifluoro-m-tolualdehyde (3.63 g, 0.021 mol) was added neat to 4-bromo-3-trifluoromethylaniline (5.0 g, 0.021 mol). Dichloroethane (50 mL) was added followed by sodium triacetoxyborohydride (4.85 g, 0.023 mol) and acetic acid (1.42 g, 0.024 mol). The resulting mixture was stirred at room temperature for 18 h, then diluted with methylene chloride, quenched with sodium bicarbonate and extracted with methylene chloride. The organic layers were combined and dried over MgSO4 and concentrated to give 6.97 g of the desired 3-[4-bromo-3-(trifluoromethyl)-phenyl[[3-(trifluoromethyl)phenyl]methyl]amine product as a yellow oil, which was carried forward without purification. ESMS m/z=397 [M+H]+.

According to the analysis of related databases, 393-36-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sikorski, James A.; Durley, Richard C.; Mischke, Deborah A.; Reinhard, Emily J.; Fobian, Yvette M.; Tollefson, Michael B.; Wang, Lijuan; Grapperhaus, Margaret L.; Hickory, Brian S.; Massa, Mark A.; Norton, Monica B.; Vernier, William F.; Parnas, Barry L.; Promo, Michele A.; Hamme, Ashton T.; Spangler, Dale P.; Rueppel, Melvin L.; US2002/120011; (2002); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 328-70-1,Some common heterocyclic compound, 328-70-1, name is 1-Bromo-3,5-bis(trifluoromethyl)benzene, molecular formula is C8H3BrF6, 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: Inside an argon atmosphere glove box, halide (0.5mmol), boronic acid (0.75mmol), K3PO4 (1.5mmol), PPPd (4mg, 1.4wt% Pd, 0.0005mmol), solvent (2ml, H2O/EtOH v/v=2:3) were mixed in a 5ml vessel and sealed. Then it was moved out of the glove box and heated in an oil bath to 80C for 2-6h. After cooled down to r.t. for about half an hour, the mixture was filtered. Take a small amount of the liquid for GC analysis. The solid part was washed three times with ethanol. The combined liquid was dried and purified by column to give pure coupling product. For recycle experiments, the solid part after washing was degassed and used into the next cycle. Combing the recycled catalyst from X reaction times was marked as Re-PPPd-X.

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-3,5-bis(trifluoromethyl)benzene, its application will become more common.

Reference:
Article; Wang, Xinbo; Min, Shixiong; Das, Swapan K.; Fan, Wei; Huang, Kuo-Wei; Lai, Zhiping; Journal of Catalysis; vol. 355; (2017); p. 101 – 109;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 418762-26-2, These common heterocyclic compound, 418762-26-2, name is 4-Bromo-2-fluoro-5-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.

Part A. Preparation of N-(4-bromo-2-fluoro-5-methylphenyl)methanesulfonamide.; [0073I]To a solution of 4-bromo-2-fluoro-5-methylaniline (2.04 g, lO.Ommol) in anhydrous CH2Cl2(20ml) and pyridine (3.23ml, 40.0mmol) was added methanesulfonyl chloride (0.86ml, 1 l.Ommol) and the resulting mixture was stirred at room temperature for 2h. Solvent was removed in vacuo, and the residue was partitioned between EtOAc and IM aq. HCl. The organic layer was washed with saturated aqueous NaHCO3, brine and then dried over Na2SO4. The drying agent was filtered off, and the filtrate was concentrated to give the title compound as a solid (2.80 g, 99%).

The synthetic route of 418762-26-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBOTT LABORATORIES; WO2009/39135; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 630-17-1,Some common heterocyclic compound, 630-17-1, name is 1-Bromo-2,2-dimethylpropane, molecular formula is C5H11Br, 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.

Diisopropyl(2,2-dimethylpropyl)silane (51a) Magnesium (2.43 g, 100 mmol) and iodine (catalytic amount) were added to THF (100 mL), and 1-bromo-2,2-dimethylpropane (10.7 mL, 100 mmol) was added dropwise thereto for 20 minutes, followed by stirring at room temperature for 1 hour. After termination of exothermic reaction, the resultant mixture was further stirred at 50C for 5 hours, whereby 2,2-dimethylpropylmagnesium bromide THF solution was prepared. The procedure of synthesizing Compound 47a was repeated, except that the thus-prepared mixture was employed, whereby the Compound 51a was obtained as a colorless liquid (boiling point; 40 mmHg, 120.0 to 122.5C fraction, 7.65 g, 45%). 1H-NMR(CDCl3)delta 3.60 (1H, br s), 1.03-0.85 (23H, m), 0.67-0.63 (2H, m).

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-2,2-dimethylpropane, its application will become more common.

Reference:
Patent; TAIHO PHARMACEUTICAL COMPANY LIMITED; Sasaki, Takuma; Matsuda, Akira; EP1845102; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 45762-41-2, name is 4-Bromo-2-ethylaniline, 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 45762-41-2, name: 4-Bromo-2-ethylaniline

A solution of 4-bromo-2-ethylaniline (200 mg) in dichloromethane (10 mL) was treated with 1-fluoro-2-isocyanato-4-methylbenzene (151 mg), stirred at room temperature overnight, diluted with hexanes, and filtered. The filter cake provided 227 mg of the desired product. MS (ESI(+)) m/e 351,353 (M+H)+.

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; Dai, Yujia; Davidsen, Steven K.; Ericsson, Anna M.; Hartandi, Kresna; Ji, Zhiqin; Michaelides, Michael R.; US2004/235892; (2004); 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. 3875-78-3, name is 6-Bromochroman, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 3875-78-3

To a mixture of 6-bromochromane (2.0 g, 9.43 mmol, 1.00 equiv) in THF (20 ml_) was added n-BuLi (2.5 M in hexane, 3.76 ml_, 1.00 equiv) dropwise at – 78C. The reaction mixture was stirred at -78C for 30 min. To the mixture was then added a solution of 4-(benzyloxy)-5-bromo-2-methoxybenzaldehyde (2.74 g, 8.56 mmol, 0.91 equiv) in THF (2 ml_) dropwise at -78C. The reaction mixture was stirred for 2 h at -78C. NH4CI/H2O was added and the mixture was extracted with EtOAc thrice. The combined extracts were washed with brine and dried over Na2SC>4. The mixture was concentrated and the resulting residue purified by chromatography on silica gel (3: 1 PE/EA) to yield (4-(benzyloxy)-5-bromo-2-methoxyphenyl)(chroman-6-yl)methanol as a colorless oil.

According to the analysis of related databases, 3875-78-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; GUOZHANG, Xu; KUO, Gee-Hong; GAUL, Micheal; (163 pag.)WO2019/215633; (2019); 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. 502496-36-8, name is 3-Bromo-5-fluoro-2-methylaniline, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C7H7BrFN

To a solution of 3-bromo-5-fluoro-2-methyl-phenylamine (470mg) in dioxane (6 mL) was added triethylamine (1.28 mL), palladium acetate (25 mg), 2-dicyclohexylphosphino biphenyl (161mg) and pinacol borane (1.001ml) and the mixture was heated to 8O0C for 4 h. The reaction mixture was cooled, diluted with chloroform, washed with brine, dried (MgSO4) and the solvent removed in vacuo. The residue was purified using flash chromatography to yield 45 (466 mg).

According to the analysis of related databases, 502496-36-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GENENTECH, INC.; F. HOFFMANN – LA ROCHE AG; WO2009/42607; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 348-57-2, A common heterocyclic compound, 348-57-2, name is 1-Bromo-2,4-difluorobenzene, molecular formula is C6H3BrF2, 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.

General procedure: NHC-PdMNPs nanomagnetic catalyst (0.15 mol% Pd),aryl halide (1.0 mmol), phenylboronic acid (1.1 mmol) andpotassium carbonate (2.2 mmol) were placed in a roundbottomedflask. To the mixture, EtOH:H2O (1:1, 5 mL) wasadded and stirred at 70 C for various times. The progressof the reaction was monitored by TLC. After reaction completion,the mixture was cooled to room temperature andthe NHC-PdMNPs nanomagnetic catalyst was separatedby using an external magnet. To the filtrate, ethyl acetate(10 mL) and water (10 mL) were added. Ethyl acetate layerwas separated from the water layer using a separatory funneland dried with sodium sulphate. The dried ethyl acetatewas concentrated in vacuo and the product was purifiedby column chromatography using n-hexane and ethylacetate as eluents to afford the corresponding products ingood to excellent yields. All the coupling products wereknown molecules and were confirmed by comparing the melting point, 1H NMR and mass spectroscopic data withthe authentic samples.

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; Vishal; Fahlman, Bradley D.; Sasidhar; Patil, Shivaputra A.; Patil, Siddappa A.; Catalysis Letters; vol. 147; 4; (2017); p. 900 – 918;,
Bromide – Wikipedia,
bromide – Wiktionary