Author: tianli

Adding a certain compound to certain chemical reactions, such as: 25574-11-2, 3-(4-Bromophenyl)propan-1-ol, 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, Formula: C9H11BrO, blongs to alcohols-buliding-blocks compound. Formula: C9H11BrO

To a solution of 3-(4-bromophenyl)propan-l-ol (22.8 g, 106 mmol, 1 equiv.) in THF (1.06 L) at -78C was added w-BuLi (1.6 M, 358 mL, 573 mmol, 5.4 equiv.) dropwise. After stirring at -78C for 5 hours, the temperature was allowed to reach -50C and isobutylene oxide (47.1 mL, 530 mmol, 5 equiv.) was added dropwise. After stirring at -50C for 30 min, boron trifluoride etherate (101 mL, 796 mmol, 7.5 equiv.) was added dropwise. After stirring at -50C for lh30, the reaction was quenched with a 10% w/w solution of Na/K tartrates and the mixture was allowed to reach room temperature overnight. It was extracted three times with ether, the combined organic extracts were dried over sodium sulfate and the solvent was evaporated. Lighter impurities were removed by bulb-to-bulb distillation (100-120C, 10 mbar) to afford 3-[4-(2-hydroxy-2- methylpropyl)phenyl]propanol as an oil (11.5 g, 52 % yield) that solidified upon standing. 1H NMR: 1.22 (s, 6H), 1.44 (s, 2H), 1.85-1.92 (m, 2H), 2.65-2.73 (m, 2H), 2.73 (s, 2H),3.67 (t, / = 6.4, 2H), 7.12-7.14 (m, 4H). 13C NMR: 140.0 (s), 135.2 (s), 130.5 (d, 2C), 128.3 (d, 2C), 70.8 (s), 62.3 (t), 49.3 (t), 34.2 (t), 31.7 (t), 29.2 (q, 2C).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,25574-11-2, 3-(4-Bromophenyl)propan-1-ol, and friends who are interested can also refer to it.

Reference:
Patent; FIRMENICH SA; COULOMB, Julien; (28 pag.)WO2017/9175; (2017); A1;,
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Related Products of 612-16-8, 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 612-16-8 as follows.

In the glove box, Mn(CO)5Br (0.005mmol), [(E)-2-(2-(1-(2-pyridyl)ethylidene)-indenyl)pyridinium](0.006 mmol),Add 1.0 mL of toluene, stir for two hours, add 2-methylquinoline 4 (2 mmol),2i (1 mmol), after reacting at 135 C for 48 hours, the reaction was stopped, and the solvent was evaporated to dryness.Column chromatography ethyl acetate / petroleum ether (1:10),Trans-disubstituted olefin derivative 3ai. The product was a white solid with a yield of 93%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,612-16-8, its application will become more common.

Reference:
Patent; Qingdao University of Science and Technology; Zhang Chunyan; (19 pag.)CN108250153; (2018); A;,
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Synthetic Route of 1462-03-9, 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. 1462-03-9, name is 1-Methylcyclopentanol. A new synthetic method of this compound is introduced below.

1-methylcyclopentanol (2 mmol), catalytic amounts of the ionic liquid, and 1-2 mL of acetic acid were charged into an oven-dried Schlenk tube under nitrogen. The reaction mass was stirred for 15-20 minutes at r.t. before adding the selected nitrile (1 mmol). The reaction mass was stirred at the indicated temperature for the specified time (see Table 3). The progress of the reaction was monitored by TLC and GC-MS. After completion of reaction, the reaction mass was quenched with distilled water followed by neutralization with dilute NaHCO3 solution. The product was extracted with diethyl ether, dried over anhydrous MgSO4, and the ether layer was evaporated in vacuum. The resulting crude products were chromatographed with hexane-ethyl acetate mixture (80:20) to afford pure colorless solids.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1462-03-9, its application will become more common.

Reference:
Article; Kalkhambkar, Rajesh G.; Waters, Sarah N.; Laali, Kenneth K.; Tetrahedron Letters; vol. 52; 8; (2011); p. 867 – 871;,
Alcohol – Wikipedia,
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Application of 7073-69-0 , The common heterocyclic compound, 7073-69-0, name is 2-(2-Bromophenyl)propan-2-ol, molecular formula is C9H11BrO, 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 2[00253] To a solution of n-BuLi (21.2ml, 0.053 mol) in anhydrous THF (160 mL) at – 78C under argon was slowly added a solution of 2-(2-bromophenyl)propan-2-ol (XCV) (0.0212 mol, 4.55 g) in anhydrous THF (50 mL) while maintaining the temperature below -65C. After addition was complete, the reaction mixture was stirred at -75C for 30 min. To this mixture was added in portions trimethyl borate (0.032mol, 3.3 g), and the reaction mixture was stirred at – 78C for 30 min and then at room temperature overnight. The mixture was cooled to 0C, carefully quenched with 1M aqueous HCl, and stirred at room temperature for 15 min. The mixture was acidified to pH 3 with 2M HCl and stirring was continued for 1 hour. The two phases were separated and the aqueous layer was extracted with EtOAc. The combined organic phases were dried over MgS04. The crude product was purified by silica gel chromatography using DCM followed by DCM/MeOH 300/1 to give 3,3-dimethylbenzo[c][l,2]oxaborol-l(3H)- ol (XCVI) as a light yellow oil (1.37 g; 8.5 mmol, 40% yield). 1H NMR (CDC13) delta ppm 1.54 (s, 6H), 7.25-7.29 (m, 1H), 7.33 (d, J=7Hz, 1H), 7.45 (td, J=7Hz, J=lHz, 1H), 7.68 (d, J=7Hz, 1H).

The synthetic route of 7073-69-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; REMPEX PHARMACEUTICALS, INC.; GLINKA, Tomasz; HIGUCHI, Robert; HECKER, Scott; EASTMAN, Brian; RODNY, Olga; WO2012/109164; (2012); A1;,
Alcohol – Wikipedia,
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The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 6642-34-8, name is (6-Bromobenzo[d][1,3]dioxol-5-yl)methanol. This compound has unique chemical properties. The synthetic route is as follows. Formula: C8H7BrO3

To a stirred solution of (6-bromo-1,3-benzodioxol-5-yl)methanol (1.27 g, 5.50 mmol) in THF (45.0 ml.) was added n-BuLi (5.00 ml_, 2.0 M, 10.0 mmol) dropwise at -75 0C. The reaction mixture was stirred at -75 0C for 45 min followed by the addition of a solution of 1-pentyl-1/-/-indole-2,3-dione (1.00 g, 4.60 mmol) in THF (20.0 ml.) at -75 0C. The resulting mixture was stirred at ambient temperature for 12 hrs and quenched with ammonium chloride solution (5.00 ml_). More ethyl acetate and water were added and separated. The organic layer was concentrated in vacuo to dryness. The residue was subjected to column chromatography eluting with 50% EtOA?Hexanes to yield the title compound (0.29 g, 25%) as a solid: 1H NMR (300 MHz, CDCI3) delta 7.38-7.24 (m, 2H), 7.11 (t, 1 H), 6.91 (d, 1 H), 6.81 (s, 1 H), 6.43 (s, 1 H), 5.90-5.87 (m, 2H), 4.77 (dd, 2H), 3.75-3.56 (m, 2H), 1.75-1.58 (m, 2H), 1.26-1.35 (m, 2H), 0.89-0.83 (m, 3H); 13C NMR (75 MHz, CDCI3) delta 177.8, 147.4, 147.2, 142.8, 133.5, 132.2, 131.1 , 130.1 , 125.3, 123.8, 111.4, 109.2, 108.1 , 101.5, 79.5, 64.7, 40.4, 29.0, 26.8, 22.3, 13.9; MS (ES+) m/z 352.1 (M – 17).

With the rapid development of chemical substances, we look forward to future research findings about 6642-34-8.

Reference:
Patent; XENON PHARMACEUTICALS INC.; WO2006/113864; (2006); A2;,
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Reference of 4728-12-5 ,Some common heterocyclic compound, 4728-12-5, molecular formula is C7H14O3, 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.

30.1.(2,2-dimethyl-1,3-dioxan-5-yl)methyl 4-methylbenzenesulfonateTo a solution of 1.5 g (10.26 mmol) of (2,2-dimethyl-1,3-dioxan-5-yl)methanol and 1.71 mL of Et3N in 15 mL of DCM, cooled to 0° C., are added 2.15 g (11.3 mmol) of tosyl chloride.The medium is allowed to warm to room temperature, and stirring is continued for 1 hour.The medium is taken up in 100 mL of DCM, washed successively with 0.1N HCl (2*20 mL) and brine (20 mL), dried over Na2SO4, concentrated under reduced pressure and then purified by chromatography on a column of silica gel, eluting with a 99/1 DCM/MeOH mixture.3 g of (2,2-dimethyl-1,3-dioxan-5-yl)methyl 4-methylbenzenesulfonate are obtained in the form of a colourless oil.Yield=97percent1H NMR, CDCl3, 400 MHz, delta (ppm): 7.8 (d, 2H); 7.3 (d, 2H); 4.1 (d, 2H); 3.9 (dd, 2H); 3.6 (dd, 2H); 2.4 (s, 3H); 1.9 (m, 1H); 1.4 (s, 3H); 1.2 (s, 3H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4728-12-5, its application will become more common.

Reference:
Patent; SANOFI; US2011/294788; (2011); A1;,
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With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.153599-45-2, name is Methyl 3-(2-hydroxyethyl)benzoate, molecular formula is C10H12O3, molecular weight is 180.2, as common compound, the synthetic route is as follows.Computed Properties of C10H12O3

To a stirred solution of methyl 3- (2-hydroxyethyl) benzoate (10 g) in anhydrous dichloromethane (90 mL) at 0 C was added methanesulfonyl chloride (34 g, 299 mmol) And triethylamine (12 g, 118 mmol).The reaction was stirred at 0 C for 1 hour, quenched with water (50 ml)And extracted with ethyl acetate (100 ml x 3). The combined organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: 10% ethyl acetate in petroleum ether)To give 2.7 g of methyl 3- (2 – ((methylsulfonyl) oxy) ethyl) benzoate as a colorless oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,153599-45-2, Methyl 3-(2-hydroxyethyl)benzoate, and friends who are interested can also refer to it.

Reference:
Patent; CHIA TAI TIANQING PHARMACEUTICAL GROUP CO., LTD.; DING, ZHAO ZHONG; WU, HAO; SUN, FEI; WU, LI FANG; YANG, LING; (97 pag.)TWI558709; (2016); B;,
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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. 13826-35-2, name is (3-Phenoxyphenyl)methanol, molecular formula is C13H12O2, The 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. Computed Properties of C13H12O2

Manufacturing Example 28-1: 1-Chloromethyl-3-phenoxy-benzene To a solution of carbon tetrachloride (40 mL) of (3-phenoxy-phenyl)-methanol (2.0 g) was added triphenylphosphine (3.2 g) at room temperature, which was heated to reflux under a nitrogen atmosphere for 5 hours and 40 minutes. The reaction mixture was cooled to room temperature and the solvent was evaporated under a reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethyl acetate = 10:1) to obtain the titled compound (2.1 g). 1H-NMR spectrum (DMSO-d6) 8 (ppm): 4.37 (2H, s), 6.94-6.97 (1H, m), 7.00-7.03 (2H, m), 7.05-7.06 (1 H, m), 7.13-7.20 (3H, m), 7.37-7.41 (2H, m).

With the rapid development of chemical substances, we look forward to future research findings about 13826-35-2.

Reference:
Patent; Eisai R&D Management Co., Ltd.; EP2065377; (2009); A1;,
Alcohol – Wikipedia,
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Synthetic Route of 42822-86-6, Adding some certain compound to certain chemical reactions, such as: 42822-86-6, name is 2-(2-Hydroxypropan-2-yl)-5-methylcyclohexanol,molecular formula is C10H20O2, 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 42822-86-6.

General procedure: para-Methane-3,8-diol (3, 5.0 g, 0.029 mol) and an appropriatemolar equivalence of acid anhydride were transferred into thereactor concurrently. Both reagents were stirred and heated at60 Cfor 10 minutes. The homogeneous mixture was achievedand 0.3 g of polymer-bound scandium triflate (PS-Sc(OTf)3)catalyst was added into the reaction mixture. The reaction wasstirred 60 Cfor 24 hours, while followed by sampling at anhourly interval. Upon the completion of the reaction, the catalyst was separated from the product mixture by filtration and theacid was removed by distillation. The obtained crude samplewas purified by column chromatography hexane/EtOAc (98:2).The colourless oily products were analysed.

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. 42822-86-6, 2-(2-Hydroxypropan-2-yl)-5-methylcyclohexanol, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Mafu, Lubabalo; Zeelie, Ben; Watts, Paul; Beilstein Journal of Organic Chemistry; vol. 12; (2016); p. 2046 – 2054;,
Alcohol – Wikipedia,
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Application of 7250-55-7, 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 7250-55-7 as follows.

To a stirred solution of dimethyl 3-hydroxyglutarate (19.98 g, 113.4mmol) in THF (340 mL) under argon at room temperature was added BH3·Me2S (3 equiv., 32.26 mL, 340.1 mmol) drop to drop. After 48 h the reaction mixture was diluted with MeOH (340 mL) with intense formation of bubbles, and stirred morefor 1 h. The solvent was distilled off and the residue purified by column chromatography on silica gel (EtOAc to MeOH/EtOAc, 1:9) to afford pentane-1,3,5-triol (2) (12.30g, 90%) as a colorless oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,7250-55-7, its application will become more common.

Reference:
Article; Kang, Young-Goo; Park, Chan-Yong; Shin, Hongsuk; Singh, Ramandeep; Arora, Garima; Yu, Chan-Mo; Lee, Ill Young; Bioorganic and Medicinal Chemistry Letters; vol. 25; 17; (2015); p. 3650 – 3653;,
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