Tag: M.W=200-300

Application of 5467-58-3,Some common heterocyclic compound, 5467-58-3, name is 1-Bromo-4-methoxynaphthalene, molecular formula is C11H9BrO, 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-a. Synthesis of 1-methoxy-4-{4-(naphthalen-2-yl)phenyl}naphthalene 1-Methoxy-4-{4-(naphthalen-2-yl)phenyl} was synthesized as follows. 1-Bromo-4-methoxynaphthalene (25 g, 0.105 mol), 4-(naphthalen-2-yl)phenylboronic acid (30.4 g, 0.137 mol), potassium carbonate (21.9 g, 0.16 mol), tetrakis(triphenylphosphine)palladium(0) (2.4 g, 0.01 mol), water (25 mL), tetrahydrofuran (75 mL) and toluene (75 mL) were stirred in a 250 mL round-bottom flask for 12 hours under reflux. After completion of the reaction, the reaction mixture was cooled to room temperature and extracted with ethyl acetate (300 mL) and water (1000 mL). The organic layer was dried with magnesium sulfate and concentrated under reduced pressure. The resulting solid was dissolved in hot toluene (400 mL) and filtered. The filtrate was recrystallized in methanol (800 mL). The resultant solid was filtered and washed with hexane (300 mL) to obtain a product (26 g, 0.072 mol, 68.4%).

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-methoxynaphthalene, its application will become more common.

Reference:
Patent; SFC CO., LTD.; US2011/108827; (2011); A1;,
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Synthetic Route of 59557-91-4,Some common heterocyclic compound, 59557-91-4, name is 4-Bromo-2-methoxyaniline, molecular formula is C7H8BrNO, 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-methoxyaniline (50.0 g, 247 mmol) was added to a mixture of sodium 3- nitrobenzenesulfonate (86.8 g, 385 mmol) and propane-1 ,2,3-triol (108 g, 1 .18 mol) in cone. H2SO4 (97 ml.) and water (75.7 ml.) at 0 C over a period of 30 min under nitrogen. After stirring at 120 C for 24 h and then cooling to RT, the reaction mixture was quenched slowly with 2M NaOH (1 L). The aq. solution was extracted with EtOAc (3 x 500 ml_). The combined organic phases were dried over Na2S04, filtered and concentrated to afford 6-bromo-8- methoxyquinoline (Intermediate 49, 60.0 g, 100%); M/Z (ES+), [M+H]+= 237.1H NMR (300 MHz, DMSO-ofe) delta 3.99 (s, 3H), 7.30 (d, 1 H), 7.58-7.60 (m, 1 H), 7.79 (s, 1 H), 8.28 (dd, 1 H), 8.86 (dd, 1 H).

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

Reference:
Patent; ASTRAZENECA AB; PACKER, Martin, John; PERKINS, David, Robert; SWALLOW, Steven; HIRD, Alexander; YE, Qing; PENG, Bo; ZHENG, Xiaolan; JOHANNES, Jeffrey; MLYNARSKI, Scott; LAMB, Michelle; HUYNH, Hoan; ROBBINS, Daniel, William; (182 pag.)WO2018/178226; (2018); A1;,
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Related Products of 588-63-6, 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. 588-63-6, name is (3-Bromopropoxy)benzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

0.3 g (0.00089 mol) of N- [ (3R)-1-azabicyclo [2.2. 2] [OCT-3-YL]-9H-XANTHENE-9-CARBOXAMIDE] (Example 31) were dissolved in 6 [ML] of THF. To this solution 0.21 ml (0.287g, 0.001335 mol) of [(3-BROMOPROPOXY)] benzene were added. The mixture was refluxed during 4 hours and then stirred 17 h at room temperature. The reaction mixture was filtered and the solid obtained washed with ether several times and dried. 0.48 [G] (98percent) of the title product were obtained. m. p.: 278.5-279. [2C] [MS [M-BR] + :] 469 [APOS;H-NMR] (DMSO-d6) : [S] 1.80-2. 0 (m, 3H), 2.05-2. 30 (m, 4H), 3.15-3. 25 (m, [1H),] 3.30-3. 65 (m, 6H), 3.82 (m, [1H),] 4.05 (t, 2H), 4.10 (m, [1H),] 5.05 (s, [1H),] 6.90-7. 0 (m, 3H), 7.05-7. 20 (m, 4H), 7.25-7. 42 (m, 6H), 9.01 (d, [1H,] NH).

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-Bromopropoxy)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ALMIRALL PRODESFARMA S.A.; WO2004/5285; (2004); A1;,
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Adding a certain compound to certain chemical reactions, such as: 175278-17-8, name is 2-Bromo-4-(trifluoromethoxy)aniline, 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 175278-17-8, Formula: C7H5BrF3NO

General procedure: 1,1-Cyclopropanedicarboxylic acid (5) (12.0 g, 15.4 mmol) was dissolved in anhydrous THF (50 mL). Then triethanolamine (2.0 mL,13.9 mmol) was added to the mixture and the mixture was stirred on the ice-bath for 30 min. SOCl2 (1.2 mL, 16.66 mmol) was then added. Stirring was continued for 2h, a solution of 3,5-dimethylaniline 6 (3.6 g, 15.4 mmol) in anhydrous THF (10 mL) was added and continued stirring for 2h, after that, the ice bath was removed, and the mixture was stirred at room temperature overnight. After the completion of the reaction, the mixture was filtered and concentrated in vacuo. The residues was purified by silica gel flash chromatography (PE/AcOEt = 5:1) to yield 7 as white solid (0.8 g, 30.7%).

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-4-(trifluoromethoxy)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Li, Chuansheng; Shan, Yuanyuan; Sun, Ying; Si, Ru; Liang, Liyuan; Pan, Xiaoyan; Wang, Binghe; Zhang, Jie; European Journal of Medicinal Chemistry; vol. 141; (2017); p. 506 – 518;,
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Related Products of 6358-77-6, These common heterocyclic compound, 6358-77-6, name is 5-Bromo-2-methoxyaniline, 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.

Step 1. Synthesis of 1 -(5-bromo-2-methoxyphenyl)-5-methyl-1 H-pyrazole (C14). Boron trifluoride-tetrahydrofuran complex (777 g, 5.55 mol) was slowly added to a solution of 5-bromo-2-methoxyaniline (799.8 g, 3.96 mol) in 2-methyltetrahydrofuran (5.3 L), and the mixture was filtered through Celite. The filtrate was brought to a volume of 9 L with additional 2-methyltetrahydrofuran. In a separate container, tert-butyl nitrite (433 g, 4.20 mol) was dissolved in 2-methyltetrahydrofuran (8.0 L); the volume was then adjusted to 9 L by addition of 2-methyltetrahydrofuran. The two solutions were pumped by two Ismatec syringe pumps, both of which had been calibrated to deliver 15 mL/minute of 2-methyltetrahydrofuran, into a T-mixer connected to a 240 ml_ polytetrafluoroethylene (PTFE) coil for diazonium salt formation. At a combined flow rate of 30 mL/minute, the reaction mixture had a total residence time of 8 minutes in the coil to facilitate complete diazonium salt formation. The syringe pumps were started simultaneously, and the material was passed through the coil into a two-stage continuous flow stirred-tank reactor, where the 5-bromo-2-methoxybenzenediazonium tetrafluoroborate product (C12) was continuously extracted into water, using a water pump with a flow rate of 20 to 22.5 mL/minute. The aqueous layer was continuously separated in a stand pipe decanter, and then quenched into a jacketed 20 L reactor containing a mixture of tin(ll) chloride dihydrate (2.28 kg, 12.0 mol), 2- methyltetrahydrofuran (4 L) and water (4 L) at zero C. When the reduction had provided complete conversion to (5-bromo-2-methoxyphenyl)hydrazine (C13), as monitored by HPLC analysis, a solution of (3E)-4-(dimethylamino)but-3-en-2-one (454 g, 4.01 mol) in 2-methyltetrahydrofuran (3.0 L) was charged, and the jacket temperature was adjusted to 20 C. After 14 hours, analysis of the organic layer indicated that hydrazine C13 had been consumed. The layers were separated, and the organic layer was washed with aqueous sodium hydroxide solution (6 N, 2 x 5 L). Silica gel (1 .0 kg) was added to the organic phase, and the mixture was concentrated to dryness and dried at 35 C and 100 mbar vacuum on a rotary evaporator until a free-flowing powder was obtained. This powder was loaded onto a pad of silica gel (100 g), and elution was carried out with 2- methyltetrahydrofuran (6 L); the eluant was concentrated in vacuo to provide the product as a thick dark red oil. 1H NMR data indicated that this material was comprised of a roughly 9:1 ratio of the title product and the regioisomeric pyrazole. Yield: 573 g, 2.15 mol, 67% (corrected for 80% purity of starting 5-bromo-2-methoxyaniline). GCMS m/z 266, 268 (M+). 1H NMR (400 MHz, CDCI3) title product peaks only: delta 7.60 (d, J=1 .8 Hz, 1 H), 7.52 (dd, half of ABX pattern, J=8.7, 2.4 Hz, 1 H), 7.49 (d, half of AB pattern, J=2.4 Hz, 1 H), 6.92 (d, J=8.7 Hz, 1 H), 6.16-6.18 (m, 1 H), 3.79 (s, 3H), 2.16 (br s, 3H).

Statistics shows that 5-Bromo-2-methoxyaniline is playing an increasingly important role. we look forward to future research findings about 6358-77-6.

Reference:
Patent; PFIZER INC.; BRODNEY, Michael Aaron; WO2012/172449; (2012); A1;,
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Electric Literature of 36805-97-7, 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 36805-97-7 as follows.

A solution of 4-carboxybenzaldehyde (15A) (0.35 g, 2.1 mmol) in toluene (9 mL) was heated to reflux and N,N-dimethylformamide di-tert-butyl-acetal (3.8 mL, 16.0 mmol) was added over 25 minutes. After the addition was complete, the reaction was stirred at reflux for an additional hour then cooled to room temperature. The reaction mixture was washed sequentially with water, 5% aqueous NaHCO3, and brine. The organic phase was separated, dried over MgSO4, filtered and concentrated in vacuo to provide compound 16A, which was used without further purification (0.37 g, 45%).

According to the analysis of related databases, 36805-97-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SCHERING CORPORATION; WO2008/130584; (2008); A1;,
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Application of 17715-69-4, The chemical industry reduces the impact on the environment during synthesis 17715-69-4, name is 1-Bromo-2,4-dimethoxybenzene, I believe this compound will play a more active role in future production and life.

General procedure: To a flask containing Mg turnings (0.29 g, 12 mmol) was added1-bromo-4-methylbenzene (1.37 g, 8.0 mmol) in THF (8 mL) at room temperature. After being stirred for 2 h, DMF (1.3 mL,12 mmol) was added to the reaction mixture. The obtained mixturewas stirred for 2 h at 0 ° C. Then, aq NH3 (7 mL, 28-30percent) and I2 (4.06 g, 16 mmol) were added to the reaction mixture. After beingstirred for 2 h at room temperature, the reaction mixture waspoured into satd aq Na2SO3 solution and was extracted with CHCl3 (3*30 mL). The organic layer was dried over Na2SO4 and filtered.After removal of the solvent, the residue was purified by shortcolumn chromatography on silica gel (eluent: hexane/ethylacetate=9:1, v/v) to provide pure 4-methyl-1-benzonitrile (0.77 g) in 82percent yield.

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, 1-Bromo-2,4-dimethoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Ishii, Genki; Harigae, Ryo; Moriyama, Katsuhiko; Togo, Hideo; Tetrahedron; vol. 69; 5; (2013); p. 1462 – 1469;,
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Related Products of 168268-00-6, 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. 168268-00-6, name is 4-(Benzyloxy)-3-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows.

To a suspension of 4-(benzyloxy)-3-fluoroaniline (1.04 g, 4.8 mmol) (WO 2005030140) under a nitrogen atmosphere was added acetic acid (2.3 ml_, 38.3 mmol), triethy lorthoformate (2.44 ml_, 14.4 mmol) and sodium azide (0.34 g, 5.3 mmol), and the reaction mixture heated at 95 C for 2.5 hours. The solution was then allowed to cool to room temperature, and water was added followed by extraction with ethyl acetate three times. The extracts were combined and washed with brine and dried over magnesium sulfate. The mixture was filtered and concentrated under reduced pressure, and the crude material purified by chromatography on silicon gel (20 – 40 % ethyl acetate in heptane) to give the title compound as a white solid (1.12 g, 86 %). 1H NMR (400 MHz, deuteromethanol) delta 9.65 (s, 1 H), 7.73 – 7.68 (dd, 1 H, J=1 1 , 2.5 Hz), 7.60 – 7.57 (m, 1 H) 7.47 – 7.45 (m, 2H), 7.40 – 7.30 (m, 5H), 5.24 (s, 2H); LCMS (ES+): 271 .1 (M+1 ).

The chemical industry reduces the impact on the environment during synthesis 4-(Benzyloxy)-3-fluoroaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; PFIZER INC.; MASCITTI, Vincent; MCCLURE, Kim Francis; MUNCHHOF, Michael John; ROBINSON, Ralph Pelton, Jr.; WO2012/69948; (2012); A1;,
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Electric Literature of 6876-00-2, 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 6876-00-2 as follows.

EXAMPLE 29 1-(2-Fluoro-3-(3-phenoxyphenyl)prop-1-enyl)-1-(2-fluoro-4-trifluoromethylphenyl) cyclopropane The method of Example 25 was repeated using a Grignard reagent, prepared from 3-phenoxyphenyl bromide (0.26 g), tetrahydrofuran (2 ml) and magnesium (22 mg) and 1-(3-acetoxy-2-fluoroprop-1-enyl)-1-(2-fluoro-4-trifluoromethylphenyl)cyclopropane (Example 21) (0.1 g). The residue after evaporation was purified by preparative thin layer chromatography (solvent: diethyl ether/hexane; 1:9) and then preparative high performance liquid chromatography (column: C8; solvent: methanol; flow rate: 2 ml/min) to afford 1-(2-fluoro-3-(3-phenoxyphenyl) prop-1-enyl)-1-(2-fluoro-4-trifluoromethylphenyl)cyclopropane (38 mg, 27%).

According to the analysis of related databases, 6876-00-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; British Technology Group Limited; US5763700; (1998); A;,
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Adding a certain compound to certain chemical reactions, such as: 60789-54-0, name is ((4-Bromobutoxy)methyl)benzene, 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 60789-54-0, name: ((4-Bromobutoxy)methyl)benzene

2-(4-benzyloxy)butyl-propanedioic acid, diethyl ester 19 To a warm solution of sodium (49.5 g, 2.15 mol) in 1 L abs. ethanol there is added diethyl malonate (325 mL, 2.11 mol). The solution is warmed up to 50 C. and crude bromide 18 (410 g, 1.68 mol) is added over a 30 m period. The mixture warms up to 65 C. and is then heated under reflux for 1 h. Most of the solvent is evaporated and to the residue there is added 1 L toluene and 500 mL water. The layers are separated and the organic layer is washed with 2*750 mL water, then dried and evaporated. The residue is purified by bulb-to-bulb distillation to afford 410 g of 19 (1.273 mol, 76%) with bp 170 C. (0.2 mmHg). This product is used as such in the next step. 1 H-NMR (CCl4): delta 1.0-2.0 (m) and 1.2 (t) (12H), 3.2(t, 1II), 3.4 (t, 2H), 4.0 (q, 4H), 4.3 (s, 2II), 7.2 (s, 5H).

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; The Horticulture and Food Research Institute of New Zealand Limited; US5677432; (1997); A;,
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