Tag: M.W=200-300

Adding a certain compound to certain chemical reactions, such as: 100751-63-1, 6-Bromo-2-naphthylmethanol, 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, SDS of cas: 100751-63-1, blongs to alcohols-buliding-blocks compound. SDS of cas: 100751-63-1

A mixture of the product from Example 1A (0.119 g, 0.50 mmol), 4 cyanophenylboronic acid (0.088 g, 0.60 mmol, 1.2 equiv.), PdCl2(PPh3)2 (7 mg, 0.001 mmol, 0.020 equiv.) and K3PO4H2O (288 mg, 1.5 mmol, 3.0 equiv.) in isopropanol (10 ML) and distilled water (4 ML) was stirred at 50 C. under a dry nitrogen atmosphere for 1.5 hr.The reaction mixture was cooled to room temperature then concentrated under reduced pressure.The residue was partitioned between ethyl acetate and saturated aqueous NH4Cl. The organic layer was dried (MgSO4), and filtered.The filtrate was concentrated under reduced pressure and the residue was purified by column chromatography (65:35 hexane/ethyl acetate).Fractions containing product were combined and concentrated under reduced pressure to provide the product as a white solid (95 mg, 73% yield). M.p. 174.1-175.5 C. 1H NMR (CDCl3, 300 MHz) delta 8.06 (d, J=2 Hz, 1H), 7.97-7.70 (m, 8H), 7.54 (dd, J=2, 12 Hz, 1H), 4.90 (dbr, J=6 Hz, 2H), 1.78 (tbr, J=6 Hz, 1H). MS (DCl-NH3) [M+NH4]+ at 277, [M+NH4 NH3]+ at 294.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,100751-63-1, 6-Bromo-2-naphthylmethanol, and friends who are interested can also refer to it.

Reference:
Patent; Altenbach, Robert J.; Black, Lawrence A.; Chang, Sou-Jen; Cowart, Marlon D.; Faghih, Ramin; Gfesser, Gregory A.; Ku, Yi-yin; Liu, Huaqing; Lukin, Kirill A.; Nersesian, Diana L.; Pu, Yu-ming; Sharma, Padam N.; Bennani, Youssef L.; US2004/92521; (2004); A1;,
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Application of 17773-10-3, 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 17773-10-3, name is Choline Iodide. This compound has unique chemical properties. The synthetic route is as follows.

CORM-338; [Me3NCH2CH2OH][Mn(CO)4I2]; 450 mg (1.40 mmol) of [Mn(CO)5I] and 301 mg (1.30 mmol) of choline iodide were stirred in 15 ml of methanol at 55 C. for 36 h. (The IR Spectrum recorded after 2 h showed a significant amount of starting material remained).Following this, the solvent was removed on a rotary evaporator to give a yellow/brown ?oily? solid. This residue was dissolved in DCM, filtered, and then diethyl ether added. This precipitated out a white solid (presumably unreacted choline iodide) which was filtered off. Solvent was then removed on a rotary evaporator and the residue again dissolved in DCM. A little hexane was then added. However, this resulted in the product separating as an oil. Hence all the solvent was removed on a rotary evaporator and the resulting semi-solid residue washed twice with diethyl ether. This produced a solid product that was dried under vacuum.405 mg (0.771 mmol) of an orange/brown solid was obtained. Mr=524.96.Yield was 59%.1H NMR (CD2Cl2): delta(ppm) 3.11 (br, OH 1H), 3.35 (br, CH3 9H), 3.68 (br, CH2 2H), 4.22 (br, CH2 2H)13O NMR (CD2Cl2): delta(ppm) 55.29 (t {J=3.9 Hz}, CH3), 56.35 (CH2), 68.16 (t {J=2.8 Hz}, CH2), 213.26 (CO), 221.91 (CO)17O NMR (CD2Cl2): delta(ppm) 377.3 (CO), 379.4 (CO)55Mn NMR (CD2Cl2): delta(ppm) -863 line width 6650 HzIR (CH2Cl2) nu(cm-1): 2077 (s), 2002 (vs), 1984 (s), 1942 (s)Mass Spec (m/z): 421 (MO), 393 (M–CO), 365 (M–2CO), 337 (M–3CO), 309 (M–4CO)Elemental: MnC9H14NO5I2 found (calc) C: 20.62 (20.59), H: 2.55 (2.69), N: 2.57 (2.67), I: 48.61 (48.35); CORM-369 (Choline][Mn(CO)4I2] [3]450 mg (1.40 mmol) of Mn(CO)5I and 301 mg (01.30 mmol) of choline iodide were stirred in 15 ml of methanol at 55 C. for 36 hrs. (IR recorded after 2 hrs showed a significant amount of starting material remaining).Following this, the solvent was removed on rotary evaporator to give a yellow/brown ?oily? solid. This residue was dissolved in DCM, filtered, and then ether added. This crashed out a white solid (presumably unreacted choline iodide) which was filtered off. Solvent was then removed on rotary evaporator and the residue again dissolved in DCM. A little hexane was then added. However, this resulted in the product crashing out as an oil. Hence all the solvent was removed on rotary evaporator and the resulting semi-solid residue washed twice with ether. This produced a solid product that was dried under vacuum.405 mg of an orange/brown solid was obtained. Yield was 59.3%.1H NMR (CD2Cl2): delta(ppm) 3.35 (br, NMe3), 3.69 (br, CH2), 4.18 (br, CH2)13C NMR (CD2Cl2): delta(ppm) 54.0 (NMe3), 56.6 (CH2), 68.5 (CH2), 211.6 (CO), 219.8 (CO),IR (CH2Cl2) nu(cm-1): 2092 (w), 2015 (vs), 1989 (s), 1943 (s)Mass Spec (m/z): 215 (M–4CO) (1:2:1 ratio of peaks observed, i.e. 79Br/81Br).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 17773-10-3, Choline Iodide.

Reference:
Patent; Motterlini, Roberto Angelo; Mann, Brian Ernest; Scapens, David Alistair; US2010/105770; (2010); A1;,
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Reference of 862135-61-3, 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. 862135-61-3, name is 5-Bromoindan-2-ol, molecular formula is C9H9BrO, 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.

A suspension of 5-bromoindan-2-ol (Combi-Blocks, cat No.QA3834: 114 mg, 0.535 mmol), potassium acetate (160 mg, 1.6 mmol) and 4,4,5,5,4′,4′,5′,5′-octamethyl-[2,2′]bi[[1,3,2]dioxaborolanyl](200 mg, 0.80 mmol) in 1,4-dioxane (2.4 mL) was first degassed with stream of nitrogen for ?5 min, then [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (1:1) (20 mg, 0.03 mmol) was added and the mixture was heated to 100 C. overnight. The reaction mixture was cooled to room temperature, concentrated then diluted with 1:1 ethyl acetate/hexanes, filtered through celite, and concentrated. The residue obtained was purified by flash chromatography on a silica gel column eluting with 0 to 40% EtOAc/Hexanes to provide the desired intermediate in nearly quantitative yield.

According to the analysis of related databases, 862135-61-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Incyte Corporation; Wu, Liangxing; Courter, Joel R.; He, Chunhong; Li, Jingwei; Lu, Liang; Sun, Yaping; Wang, Xiaozhao; Yao, Wenqing; Zhang, Colin; Zhuo, Jincong; (87 pag.)US2016/9720; (2016); A1;,
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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. 68120-35-4, name is (3-Bromo-4-methylphenyl)methanol, the common compound, a new synthetic route is introduced below. Quality Control of (3-Bromo-4-methylphenyl)methanol

To a stirred solution of (3-bromo-4-methylphenyl) methanol (5.5 g, 27.4 mmol) in THF (50 mL) at -78C, n-BuLi [(18.6 g, 2.5 eq (2.5M soln) was added and the solution was stirred at same temperature for 30 mm. Then, 002 gas was purged (generated from dry ice) for about 10 mm. The reaction mixture was quenched with ammonium5 chloride and acidified with 1 N HCI, extracted with ethyl acetate, the organic layer was washed with water, brine solution. Then, it was dried over anhydrous Na2S04 and concentrated under reduced pressure and washed with n-hexane to obtain the title compound (4.0 g, 87.85%) as an off white solid. LCMS : 165.0 (M-H) 1H NMR:(CDCI3, 300MHz) 6 12.67 (5, 1H), 7.79 (5, 1H), 7.36-7.38 (d, 1H), 7.23-7.25 (d, 1H), 10 5.23 (5, 1H), 4.49 (5, 2H), 2.50 (5, 3H).

The synthetic route of 68120-35-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; MADANAHALLI RANGANATH RAO, Jagannath; GURRAM RANGA, Madhavan; PACHIYAPPAN, Shanmugam; WO2014/202528; (2014); A1;,
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Reference of 61367-62-2, 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. 61367-62-2, name is 4-Bromo-3,5-dimethoxybenzyl alcohol. A new synthetic method of this compound is introduced below.

Production Example 12; 2-Bromo-1,3-dimethoxy-5-(methoxymethyl)benzene; Under cooling in an ice water bath, to a solution of (4-bromo-3,5-dimethoxyphenyl)methanol (118.8 g) in N,N-dimethylformamide (960 mL) was added sodium hydride (60percent oily; 24.7 g), and the mixture was stirred for 10 minutes. To this iodomethane (41.7 mL) was dropped. Thereafter, the reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into ice water (2.5 L), and extracted with ethyl acetate. The resulting organic layer was washed with saturated saline, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography, and from a fraction of n-hexane:ethyl acetate (4:1), 121.3 g of a title compound was obtained as colorless oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,61367-62-2, 4-Bromo-3,5-dimethoxybenzyl alcohol, and friends who are interested can also refer to it.

Reference:
Patent; Negi, Shigeto; Shimizu, Toshikazu; Kuroda, Hiroshi; Shimomura, Naoyuki; Sasho, Manabu; Hoshino, Yorihisa; Kubota, Manabu; US2007/191613; (2007); A1;,
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Reference of 2425-41-4, 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. 2425-41-4, name is (2-Phenyl-1,3-dioxane-5,5-diyl)dimethanol, molecular formula is C12H16O4, 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.

To a solution of 5109 (1 0.0 g, 44.6 mmol) in dichloromethane (180 ml) under argon were addedbromoacetonitrile (13.0 g, 108.4 mmol), Silver( I) oxide (20.7 g, 89.2 mmol), and tetrabutylammonium iodide (3.3 g, 8.92 mmol), and the resulting mixture was stirred overnight. The mixture was filtered overCelite, and the filtrate was evaporated to give a black residue, which was subjected to flash silica gelcolumn purification on ISCO companion (hexane/ethyl acetate, 15 – 90%) to give 5.55 g (41 %) of thedesired compound S127 as a viscous oil. ESI MS for C15H1sN204 calculated 302.3, observed [M+H]+ 303.3.

According to the analysis of related databases, 2425-41-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SOLSTICE BIOLOGICS, LTD.; SAKAMURI, Sukumar; BRADSHAW, Curt, W.; ELTEPU, Laxman; MEADE, Bryan, R.; LAM, Son; (237 pag.)WO2018/35380; (2018); A1;,
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Application of 552331-15-4, 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 552331-15-4, name is 1-(5-Bromo-2-fluorophenyl)ethanol. This compound has unique chemical properties. The synthetic route is as follows.

Step-2: Synthesis of 1-(5-bromo-2-fluorophenyl)ethan-1-one To a stirred solution of 1-(5-bromo-2-fluorophenyl)ethan-1-ol (5.3 g, 24.195 mmol, 1.0 eq) in THF (50 mL) was added Dess-martin peridionane (12.314 g, 29.034 mmol, 1.2 eq) at 0 C. The resulting mixture was stirred at rt for 15 min. The progress of reaction was monitored by LCMS. The resection mixture was quenched with saturated solution of NaHCO3 (50 mL) extracted with EtOAc (2*50 mL). The combined organic extracts were washed with water (50 mL), with brine (50 mL) dried over Na2SO4 and concentrated under reduced pressure and purified by flash chromatography [silica gel 100-200 mesh; elution 0-5% EtOAc in hexane] to afford the desired compound 1-(5-bromo-2-fluorophenyl)ethan-1-one (3.78 g, 72.00%) as yellow liquid. 1H NMR (400 MHz, CDCl3) delta 7.99 (dd, J=2.63, 6.58 Hz, 1H), 7.61 (ddd, J=2.63, 4.39, 8.77 Hz, 1H), 7.05 (dd, J=8.77, 10.09 Hz, 1H), 2.64 (d, J=4.82 Hz, 3H).

According to the analysis of related databases, 552331-15-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; giraFpharma LLC; Chakravarty, Sarvajit; PHAM, Son Minh; Kankanala, Jayakanth; AGARWAL, Anil Kumar; PUJALA, Brahmam; SONI, Sanjeev; ARYA, Satish K.; PALVE, Deepak; Gupta, Ashu; KUMAR, Varun; (498 pag.)US2019/106427; (2019); A1;,
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Reference of 722-92-9, 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.722-92-9, name is 2-(4-Aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol, molecular formula is C9H7F6NO, molecular weight is 259.15, as common compound, the synthetic route is as follows.

Intermediate 22: (R)-tert-Butyl 1-((4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)carbamoyl)-5-(methylsulfonyl)isoindoline-2-carboxylate (0745) (0746) A 2 L reactor, equipped with a thermometer, was charged with (R)-2-(tert-butoxycarbonyl)-5-(methylsulfonyl)isoindoline-1-carboxylic acid (110 g, 307.08 mmol) under nitrogen. EtOAc (1000 mL) was added and the resulting mixture was stirred for 1 min. The vessel was then charged with 2-(4-aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (84 g, 307.08 mmol), the resulting mixture was cooled to +10¡ã C. and then pyridine (27.3 mL, 337.79 mmol) was added. The reaction was cooled to +5¡ã C., and T3P (50percent in EtOAc, 274 mL, 460.62 mmol) was added at 5¡ã C. over 15 min. The temperature rose to 13.3¡ã C. over the addition, and the resulting solution was allowed to reach room temperature over 20 minutes and left stirring overnight at room temperature. The mixture was cooled to +5¡ã C., and an aqueous solution of citric acid (1N) was added, followed by 500 mL of EtOAc. Stirring was continued for 15 min, then stirring was stopped and the layers separated. The organic layer was washed with aqueous citric acid (1000 mL), and then twice with saturated aqueous NaHCO3 (1000 mL), followed by brine (1000 mL). The organic layer was separated and concentrated under reduced pressure (bath temperature 32¡ã C.). The crude material was dissolved in 550 mL of EtOH at rt, and water (440 mL) was slowly added dropwise over 15 min. Seed crystals (20 mg), were added, and the mixture was left overnight at 20¡ã C. The precipitate was isolated by filtration, washed with a 4:1 mixture of H2O/EtOH (220 mL), and dried under high vacuum. The title compound (132 g, quantitative) was used in the next step without further purification. (0747) LC/MS: m/z=581 [M?H]?, 583 [M+H]+. 1H NMR (400 MHz, DMSO-d6, mixture of rotamers, 1.9*:1) delta 1.34*, 1.46 (s, 9H), 3.20, 3.21*(s, 3H), 4.69-4.88 (m, 2H), 5.60*, 5.62 (s, 1H), 7.6-7.76 (m, 5H), 7.86-7.92 (m, 1H), 7.98, 8.01*(s, 1H), 8.68*, 8.69 (s, 1H), 10.76 (s, 1H). (0748) The seed crystals were obtained from (R)-tert-butyl 1-((4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)carbamoyl)-5-(methylsulfonyl)isoindoline-2-carboxylate (0.5 g, 0.86 mmol, prepared as described above for the large scale preparation of intermediate 22). This material was dissolved in ethanol (2.5 ml). Water (2 ml) was added until the point the mixture just became turbid. Spontaneous crystalization occurred after about 30 seconds, and (R)-tert-butyl 1-((4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)carbamoyl)-5-(methylsulfonyl)isoindoline-2-carboxylate was obtained after filtration and drying as a colorless solid (0.38 g, 76percent).

The chemical industry reduces the impact on the environment during synthesis 722-92-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; AstraZeneca AB; NARJES, Frank; OLSSON, Roine Ingemar; VON BERG, Stefan; LEVER, Sarah; (112 pag.)US2017/166527; (2017); A1;,
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Synthetic Route of 162744-59-4, Adding some certain compound to certain chemical reactions, such as: 162744-59-4, name is (4-Bromo-2,6-difluorophenyl)methanol,molecular formula is C7H5BrF2O, 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 162744-59-4.

0.7 g (7.7 mmol 10 eq) of manganese dioxide is added to a solution of 1.0 g (0.77 mmol, 1 eq) of 2,6-difluoro-4-bromobenzylalcool in 15 mL of dichloromethane. The reaction medium is stirred at room temperature for 48 hours.The solid is filtered off and the solvent is evaporated off. The residual oil is chromatographed on silica gel (8/2 heptane/ethyl acetate) and 760 mg of 4-bromo-2,6-difluorobenzaldehyde are obtained. Yield = 76%

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. 162744-59-4, (4-Bromo-2,6-difluorophenyl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GALDERMA RESEARCH & DEVELOPMENT, S.N.C.; WO2006/18326; (2006); A1;,
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Electric Literature of 149965-40-2 , The common heterocyclic compound, 149965-40-2, name is (5-Bromo-2-chlorophenyl)methanol, molecular formula is C7H6BrClO, 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: 5-Bromo-2-chlorobenzaldehyde. To a suspension of 5.23 g (23.6 mmol) of 5-bromo-2-chlorobenzyl alcohol in 50 ml of CH2Cl2 at 0 C., 8.36 g (38.7 mmol) of pyridinium chlorochromate was added. The reaction mixture was stirred at room temperature for 3 hours at which time the reaction was complete. The mixture was filtered, washed with EtOAc, dried (MgSO4), filtered, and concentrated. Flash column chromatography (10% EtOAc/hexane) yielded a pale yellow solid (4.62 g, 89%): m.p. 56-58 C.: Rf 0.73 (20% EtOAc/hexane). 1H NMR (400 MHz, CDCl3) delta7.34 (d, J=8.4 Hz, 1, ArH), 7.65 (dd, J=8.4, 2.4 Hz, 1, ArH), 8.04 (d, J=2.4 Hz, 1, ArH), 10.41 ppm (s, 1, CHO).

The synthetic route of 149965-40-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dawson, Marcia J.; Fontana, Joseph A.; Zhang, Xiao-kun; Leid, Mark; Jong, Ling; Hobbs, Peter D.; US2003/176506; (2003); A1;,
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