Tag: M.W=200-300

175278-09-8, name is 4-Bromo-2-(trifluoromethoxy)aniline, belongs to ethers-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. HPLC of Formula: C7H5BrF3NO

NaNO2 (2.43 g, 0.035 mol) in water (10 mL) was added in portions over 30 min to 4-bromo-2-trifluoromethoxyaniline (9 g, 35 mmol) in a mixture of HCl (aq, cone, 25 mL) and water (25 mL) at (0-2 0C). The mixture was stirred at 0-2 0C for 15 min and CuCl (6 g, 61 mmol) in HCl (aq, cone, 10 mL) was added dropwise. After 10 min at rt, the mixture was heated at reflux for 15 min. Steam-distillation followed by extraction (CH2Cl2), drying (Na2SO4) of the distillate followed by concentration and distillation (bp 82-84 0C at 20 Torr) gave 3.86 g (40%) of the sub-title compound.

The synthetic route of 175278-09-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOLIPOX AB; WO2006/77364; (2006); A1;,
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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 168971-68-4 as follows. Product Details of 168971-68-4

n-Butyl lithium (6.17 mL, 9.87 mmol) was added drop-wise at -78 C. to a solution of 1-bromo-2-fluoro-4-(trifluoromethoxy)benzene (2.13 g, 8.22 mmol) in diethyl ether (16.5 mL). The reaction was stirred for 30 minutes before drop-wise addition of N-methoxy-N-methylacetamide (1.272 g, 12.34 mmol). The reaction was stirred for 5 minutes at -78 C. then warmed to room temperature and stirred for 30 minutes. The solution was quenched with saturated NH4Cl, extracted with EtOAc, dried with Na2SO4, filtered, and concentrated under reduced pressure. Purification by flash silica gel chromatography, eluting with 10% EtOAc in heptanes provided 1-(2-fluoro-4-(trifluoromethoxy)phenyl)ethanone as a clear oil (1.118 g, 61%)

According to the analysis of related databases, 168971-68-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Pharmaceutical Company Limited; Hitchcock, Stephen; Lam, Betty; Monenschein, Holger; Reichard, Holly; (41 pag.)US2016/145218; (2016); A1;,
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Electric Literature of 6943-97-1, 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. 6943-97-1, name is 1-(3-Bromopropyl)-3-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows.

(16-3) Synthesis of [5-(2-{4-[3-(3-methoxyphenyl)propoxy]-3-trifluoromethylphenyl}ethyl)-2,2-dimethyl-1,3-dioxan-5-yl]carbamic acid t-butyl ester (compound 16-3) Reference Example compound 2-6 (500 mg) was dissolved in N,N-dimethylformamide (10 ml), potassium carbonate (493 mg) and compound 16-2 (328 mg) were added, and the mixture was stirred at 80C for 2 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate, washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the object product (800 mg) as a white solid. 1H-NMR(CDCl3) delta (ppm): 1.42(3H, s), 1.44(3H, s), 1.47(9H, s), 1.93-1.98(2H, m), 2.08-2.12(2H, m), 2.51-2.56(2H, m), 2.81(2H, t, J=7.5Hz), 3.69(2H, d, J=11.7Hz), 3.76(3H, s), 3.89(2H, d, J=11.7Hz), 3.99(2H, t, J=6.0Hz), 4.98(1H, brs), 6.72-6.84(4H, m), 7.19(1H, t, J=7.5Hz), 7.24(1H, d, J=1.8Hz), 7.36(1H, d, J=1.8Hz).

The chemical industry reduces the impact on the environment during synthesis 1-(3-Bromopropyl)-3-methoxybenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; EP2168944; (2010); A1;,
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Application of 588-63-6, These common heterocyclic compound, 588-63-6, name is (3-Bromopropoxy)benzene, 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: A solution of the appropriate aryloxyalkylbromides 9?16(5 mmol) commercially available or prepared as above-described,imidazole 7 or 1,2,4-triazole 8 (7.5 mmol), TEA (5 mmol) and catalyticamount of TBAB (0.1 g) in acetonitrile (3 mL) was heated undermicrowaves irradiation in a sealed vial at 100 C, 200 W, 150Psi, for 30?45 min. The solvent was removed in vacuo to give a residuewhich was suspended in water, alkalinized with NaOH 0.1 Nand extracted with dichloromethane (3 50 mL); the combinatedextracts were washed with water, dried, and evaporated to obtaina residue which was purified by flash column chromatography onsilica gel using ethyl acetate or ethyl acetate/methanol 9:1 as eluent.

The synthetic route of 588-63-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Salerno, Loredana; Pittala?, Valeria; Romeo, Giuseppe; Modica, Maria N.; Siracusa, Maria A.; Di Giacomo, Claudia; Acquaviva, Rosaria; Barbagallo, Ignazio; Tibullo, Daniele; Sorrenti, Valeria; Bioorganic and Medicinal Chemistry; vol. 21; 17; (2013); p. 5145 – 5153;,
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Application of 5414-19-7,Some common heterocyclic compound, 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane, molecular formula is C4H8Br2O, 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: Dimethyl 5-hydroxyisophthalate (1, 6 mmol), 1,omega-dialkylating agent (18 mmol) and K2CO3 (60 mmol) were stirred in anhydrous DMF (60 mL) at a room temperature for 18 h. The reaction mixture was Celite filtered, washed with dichloromethane and toluene. The combined filtrates were evaporated to dryness and the residual colorless oil was chromatographed (dichloromethane, then dichloromethane:methanol, 100:1, v/v) to give a crude product which was a white solid. The yields ranged from 18 to 80%. Some reactants prepared as above have been obtained previously by diverse methods: dimethyl 5-(2-bromoethoxy)isophthalate (2a) [11], dimethyl 5-(5-bromopentoxy)isophthalate (2b) [12] and dimethyl 5-(3-bromopropoxy)isophthalate (2d) [13].

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-bromoethoxy)ethane, its application will become more common.

Reference:
Article; Gierszewski, Mateusz; Falkowski, Michal; Sobotta, Lukasz; Stolarska, Magdalena; Popenda, Lukasz; Lijewski, Sebastian; Wicher, Barbara; Burdzinski, Gotard; Karolczak, Jerzy; Jurga, Stefan; Gdaniec, Maria; Tykarska, Ewa; Sikorski, Marek; Mielcarek, Jadwiga; Goslinski, Tomasz; Journal of Photochemistry and Photobiology A: Chemistry; vol. 307-308; (2015); p. 54 – 67;,
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Application of 59557-91-4, 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. 59557-91-4 name is 4-Bromo-2-methoxyaniline, 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.

4-Bromo-2-methoxyaniline (2.00 g, 9.90 mmol) were dissolved in water (10 mL) and concentrated hydrochloric acid (3 mL). The mixture was cooled in ice-salt bath, then a solution of sodium nitrite (0.69 g, 9.8 mmol) in water (4 mL) was added dropwise slowly while maintaining the temperature at 0-5 C. After the addition, the mixture was stirred at 0C for 5 min. The mixture described above was added to a mixture of sodium acetate trihydrate (8.75 g, 64.3 mmol), ethyl isocyanoacetate (1.0 mL, 9.15 mmol) and MeOH/H2O (22 mL, 10/1) while maintaining the temperature at 0-5 C. After the addition, the mixture was stirred at 0C for 30 min, then warmed to rt for further 3 h. After the reaction was completed, the mixture was concentrated to remove most of the solvent. The residue was filtered, and the filter cake was washed with cool water. The filter cake was dried in vacuo to give a reddish brown solid (2.65 g, 82.1%). MS (ESI, pos.ion) m/z: 327.1 (M+2)

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

Reference:
Patent; Sunshine Lake Pharma Co., Ltd.; WANG, Xiaojun; ZHOU, Pingjian; YANG, Chuanwen; HUANG, Changwei; XIONG, Shaohui; ZHANG, Yingjun; ZHANG, Jiancun; (139 pag.)EP3342765; (2018); A1;,
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Synthetic Route of 60789-54-0, A common heterocyclic compound, 60789-54-0, name is ((4-Bromobutoxy)methyl)benzene, molecular formula is C11H15BrO, 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 115 4-Amino-5-chloro-2-methoxy-N-(piperidin-4-ylmethyl)benzamide dihydrochloride (1.1 g) as starting compound, potassium carbonate (1.5 g) and 4-benzyloxybutyl bromide (1.0 g) were reacted and treated in the same manner as in Example 52 to give 0.32 g of 4-amino-5-chloro-2-methoxy-N-((1-(4-benzyloxybutyl)piperidin-4-yl)methyl)benzamide. 1H-NMR (CDCl3,ppm)delta:1.40-1.81(9H,m), 2.82(2H,t), 2.98(2H,t), 3.20(2H,t), 3.44(4H,m), 3.82(3H,s), 4.45(3H,s), 5.93(2H,s), 6.48(1H,s), 7.33-7.45(5H,m), 7.66(1H,s), 8.00(1H,t)

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; YOSHITOMI PHARMACEUTICAL INDUSTRIES, LTD.; EP873990; (1998); A1;,
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Adding a certain compound to certain chemical reactions, such as: 35822-58-3, name is 2-Bromobenzaldehyde diethyl acetal, belongs to ethers-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 35822-58-3, Safety of 2-Bromobenzaldehyde diethyl acetal

General procedure: One equiv. of protected hydrazine was dissolved/suspended in EtOH containing 10% water (approx. 5 ml per 1 mmol of protected hydrazine), 1.05 eq of benzaldehyde acetal was added, followed by the addition of 0.05 equiv. of TsOH in an ethanolic solution (10 mg of TsOH per 0.5 ml of EtOH). The obtained reaction mixture was refluxed and monitored by TLC (silica gel) until full conversion of the starting material was observed. Ethyl acetate/light petroleum mixtures or pure ethyl acetate were used as TLC eluents. After completion of the reaction the solvent was removed under reduced pressure, approx. 15 ml of toluene was added to the residue and the solvent was again removed under reduced pressure. The obtained crude hydrazone was dissolved in commercial stabilized THF (approx. 4 ml per 1mmol of hydrazone), the flask was flushed with argon and 3 equiv. of 1M BH3-THF complex was added at room temperature, followed by 3 hours of stirring. The progress of the reaction was checked by TLC and if some unreacted hydrazone was left, stirring was continued for an additional 45 min. After thefull conversion of hydrazone EtOH (10 ml) was added to the reaction mixture (Caution: Liberation of hydrogen) and the obtained mixture was refluxed for 1 hour. After cooling to room temperature the solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate, washed with saturated NaHCO3 solution, water and saturated NaCl solution. The aqueous phase was extracted twice with ethyl acetate, the extracts were washed with saturated NaCl solution, combined with the organic phase, dried over anhydrous Na2SO4 and evaporated to dryness. The residue was purified by column chromatography on silica gel by using ethyl acetate/light petroleum 1:1 or 1:2 mixtures or pure ethyl acetate as eluent. For the exact information about the eluent used for monitoring reaction progress and chromatographic purifications, see the Rf value for each compound.

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-Bromobenzaldehyde diethyl acetal, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Mastitski, Anton; Niinepuu, Siret; Haljasorg, Toiv; Jaerv, Jaak; Organic Preparations and Procedures International; vol. 50; 4; (2018); p. 416 – 423;,
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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. 101-55-3, name is 1-Bromo-4-phenoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C12H9BrO

To 260 ml toluene, 108 g para cresol and 80 g 50% caustic lye are added and the water is azeotropically distilled out. To the mass 50 ml DMF, 249 g 4-bromodiphenyl ether and 5 g CuBr are added. The mass is maintained at 150-165C for 6 hrs, cooled to 100C and filtered. The filtrate on fractional distillation gave 235 g (85% yield) of 1-(4-methytphenoxy),4-phenoxybenzene, b.p. 200-201 C/4 mm Hg pr., m.p. -53-54C

The synthetic route of 101-55-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Gharda Chemicals Limited; EP1454891; (2004); A1;,
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175278-09-8, name is 4-Bromo-2-(trifluoromethoxy)aniline, belongs to ethers-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. HPLC of Formula: C7H5BrF3NO

NaNO2 (2.43 g, 0.035 mol) in water (10 mL) was added in portions over 30 min to 4-bromo-2-trifluoromethoxyaniline (9 g, 35 mmol) in a mixture of HCl (aq, cone, 25 mL) and water (25 mL) at (0-2 0C). The mixture was stirred at 0-2 0C for 15 min and CuCl (6 g, 61 mmol) in HCl (aq, cone, 10 mL) was added dropwise. After 10 min at rt, the mixture was heated at reflux for 15 min. Steam-distillation followed by extraction (CH2Cl2), drying (Na2SO4) of the distillate followed by concentration and distillation (bp 82-84 0C at 20 Torr) gave 3.86 g (40%) of the sub-title compound.

The synthetic route of 175278-09-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOLIPOX AB; WO2006/77364; (2006); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem