Tag: M.W=200-300

Electric Literature of 722-92-9, 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. 722-92-9, name is 2-(4-Aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol. A new synthetic method of this compound is introduced below.

Step A: Preparation of 2-[1-(4-Amino-phenyl)-2,2,2-trifluoro-1-trifluoromethyl-ethoxymethyl]-pyrrolidine-1-carboxylic Acid tert-butyl Ester To a mixture of 2-(4-amino-phenyl)-1,1,1,3,3,3-hexafluoro-propan-2-ol (1.30 g), 2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (1.00 g), PPh3 (1.56 g) and molecular sieves 4 A in THF (100 mL) was added DEAD (0.93 mL) slowly.The reaction was stirred at RT for 5 h and at reflux for overnight. After filtration to remove solids, the filtrate was concentrated and the residue was taken into ether.The organic phase was washed with saturated NaHCO3 and brine.The organic layer was dried over MgSO4 and evaporated to give a crude product as a very viscous brown oil which was chromatographed through silica gel (400 g, 2:1:7 to 3:1:6 EtOAc/Et3N/hexanes) to afford 2-[1-(4-amino-phenyl)-2,2,2-trifluoro-1-trifluoromethyl-ethoxymethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester as a light brown oil. The title compound was synthesised from the above aniline in analogous to what was described previously. MS: (ES+) 654 (M+H). Calc’d. for C31H33F6N5O4-653.62.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,722-92-9, 2-(4-Aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol, and friends who are interested can also refer to it.

Reference:
Patent; Amgen Inc.; US2003/225106; (2003); A1;,
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Adding a certain compound to certain chemical reactions, such as: 20605-01-0, Diethyl 2,2-bis(hydroxymethyl)malonate, 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, 20605-01-0, blongs to alcohols-buliding-blocks compound. Computed Properties of C9H16O6

Diethyl 2,2-bis(hydroxymethyl)malonate (28.3 mmol; 6.23 g) was coevaporated twice from dry pyridine and dissolved in the same solvent (20 mL). tert-Butyldimethylsilyl chloride (25.5 mmol; 3.85 g) in dry pyridine (10 mL) was added portionwise. The reaction was allowed to proceed for 4 days. The mixture was evaporated to a solid foam, which was then equilibrated between water (200 mL) and DCM (4×100 mL). The organic phase was dried on Na2SO4. The product was purified by silica gel chromatography eluting with 10% ethyl acetate in DCM. The yield was 78%. 1H NMR (CDCl3) delta 4.18-4.25 (m, 4H, OCH2Me), 4.10 (s, 2H, CH2OSi), 4.06 (s, 2H, CH2OH), 2.63 (br s, 1H, OH), 1.26 (t, J=7.0 Hz, 6H, OCH2CH3), 0.85 (s, 9H, Si-SMe3), 0.05 (s, 6H, Me-Si). 13C NMR (CDCl3) delta 169.2 (CO), 63.3 (CH2OH), 62.8 (CH2OSi), 61.6 (spiro C), 61.4 (OCH2Me), 25.6 [C(CH3)3], 18.0 (Si-CMe3), 14.0 (OCH2CH3), -3.6 (Si-CH3). MS [M+H]+ obsd. 335.7, calcd. 335.2; [M+Na] obsd. 357.6, calcd. 357.2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,20605-01-0, its application will become more common.

Reference:
Patent; Alios BioPharma, Inc.; US2010/240604; (2010); A1;,
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Adding a certain compound to certain chemical reactions, such as: 106-28-5, (2E,6E)-3,7,11-Trimethyldodeca-2,6,10-trien-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, Recommanded Product: 106-28-5, blongs to alcohols-buliding-blocks compound. Recommanded Product: 106-28-5

Synthesis was carried out with farnesol as a starting material. The hydroxy group of farnesol was chlorinated using N-chlorosuccinimide (NCS) and dimethyl sulfide (DMS) in anhydrous dichloromethane in a nitrogen atmosphere to obtain a chloride (compound represented by (i) below) (yield: 91%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,106-28-5, (2E,6E)-3,7,11-Trimethyldodeca-2,6,10-trien-1-ol, and friends who are interested can also refer to it.

Reference:
Patent; YAMAGATA UNIVERSITY; SUMITOMO RUBBER INDUSTRIES, LTD.; Miyagi, Yukino; Ichikawa, Naoya; Ohya, Norimasa; US2014/171675; (2014); A1;,
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Reference of 355-80-6, 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 355-80-6 as follows.

In a typical experiment, 5,10,15-tris(3-acetoxyphenyl)-20-(pentafluorophenyl)-porphyrin (60.0 mg, 68.2 mupiiotaomicronGamma) was dissolved in a dry DMSO/THF (4: 1) mixture under argon atmosphere, KOH (103.4 mg, 1.84 mmol) and lH, lH,5H-octafluoropentanol (342 ml, 2.46 mmol) were added and the reaction mixture stirred under room temperature for 30 minutes. After aqueous workup, extraction with ethyl acetate and drying with Na2SO/t, the crude product was purified by column cromatography (DCM/MeOH = 95:5) and recrystallized (DCM/hexane) to obtain a purple solid (58.4 mg, 60.5 mupiiotaomicron, 88%). 5,10,15-Tris(3-hydroxy-phenyl)-20-[2,3,5,6-tetra-fluoro-4-(lH,lH,5H-octafluoro- pentyloxy)-phenyl]-porphyrin ^-NMR (500 MHz, acetone-d6): delta = -2.78 (s, 2H, NH), 5.32 (t, J = 13.8 Hz, 2H, OCH2), 6.93 (tt, J = 50.9, 5.5 Hz, 3H, CF2H), 7.30-7.34 (m, 3H, Ar-H-6), 7.62 (mc, 1H, Ar H-5), 7.62 (mc, 2H, Ar2-H-5), 7.68-7.78 (m, 6H, Ar-H-2 + Ar-H-4), 8.80-9.28 (m, 8H, ^-HPylTol) ppm. 13C-NMR (126 MHz, acetone-d6): delta = 70.3 (OCH2), 100.9 (ArF-Cmeso), 108.4 (CF2H), 115.2 (Ar-C-6), 116.4 (ArF-C,pso), 120.8 (Ar-Cmeso), 121.9 (Ar-Cmeso), 122.0 (Ar C-2), 122.0 (Ar2-C-2), 126.3 (Ar C- 4), 126.3 (Ar2-C-4), 127.8 (Ar C-5), 127.8 (Ar2-C-5), 137.4 141.4 (d, lJc.F = 246.2 Hz, ArF-CM), 142.8 (Ar2-C,pso), 143.0 (Ar C,pso), 146.9 (d, lJc.F = 241.0 Hz, ArF-Cort0), 156.0 (Ar C-3), 156.0 (Ar2-C-3) ppm. F-NMR (376 MHz, acetone-d6): delta = -121.25 – -121.42 (m, 2F, CF2), -125.24 – -125.36 (m, 2F, CF2), -130.48 – -130.62 (m, 2F, CF2), -138.95 (d, 2JH.F = 50.8 Hz, 2F, CF2H), -140.83 – -141.01 (m, 2F, Ar-Fort0), -158.30 – -158.48 (m, 2F, Ai-Fmeta) ppm. HRMS (ESI-TOF): m/z calc. for C49H29Fi2N404 [M + H]+: 965.1992; found: 965.2041 UV-VIS (acetone), Amax [log epsilon (L · mol 1 · cm”1)]: 414 (5.37), 511 (4.41), 545 (4.04), 587 (4.08), 643 (3.84) nm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,355-80-6, its application will become more common.

Reference:
Patent; BIOLITEC UNTERNEHMENSBETEILIGUNGS II AG; FREIE UNIVERSITAeT BERLIN; GOLF, Hartwig Richard Arthur; WIEHE, Arno; GRAeFE, Susanna; ALBRECHT, Volker; REISSIG, Hans-ulrich; (110 pag.)WO2016/51361; (2016); A1;,
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Electric Literature of 4654-39-1, 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 4654-39-1, name is 2-(4-Bromophenyl)ethanol. This compound has unique chemical properties. The synthetic route is as follows.

Dissolve 31.56g of iodine, 33.91g of triphenylphosphine and 22.35mg of imidazole in anhydrous dichloromethane (100mL), After 30 minutes in an ice bath, 20 g of p-bromobenzyl alcohol was dissolved in anhydrous dichloromethane (50 mL) and quickly added dropwise to the reaction bottle. Remove the ice bath and react at room temperature for about 6 hours. Dichloromethane was distilled off, the reaction liquid was transferred to a separatory funnel, a water-methanol mixed solution (400 mL, water: methanol volume ratio of 1:3) was added, n-heptane extraction (150 mL×3) was added, and shaken vigorously until The whole system is colorless and transparent, and the organic layer is combined. The organic layer was dried over anhydrous sodium sulfate, and the organic solvent was distilled off to obtain a colorless solid, that is, compound 10. The product was stored in the dark and the yield was 93.2%.

According to the analysis of related databases, 4654-39-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chinese Academy Of Medical Sciences Pharmaceutical Institute; Chen Si; Shi Zeyu; Xiao Qiong; Zhang Xiang; Tian Yulin; Yin Dali; (13 pag.)CN111087356; (2020); A;,
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Synthetic Route of 756520-66-8 , The common heterocyclic compound, 756520-66-8, name is 1-(2,6-Dichloro-3-fluorophenyl)ethanol, molecular formula is C8H7Cl2FO, 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.

In a 100mL single-necked flask,1.2 g (0.005 mol) of 2-amino-4-hydroxy-6-bromo-quinazoline was added,(0.0065 mol, 1.3 equiv) of benzotriazol-1-yloxytris (dimethylamino) phosphonium hexafluorophosphate (BOP)Acetonitrile 20 mL,Stirred at room temperature,A solution of 1.1 mL (0.0075 mol, 1.5 equiv) of 1,8-diazabicycloundecyl-7- (DBU) was added to clarify the solution,After 10min reaction with solid precipitation,Join again1.56 g of 1- (3-fluoro-2,6-dichloro-phenyl) ethanol (0.0075 mol,1.5 equiv),0.4 g of NaH (60%) and 10 mL of acetonitrile,After stirring at room temperature overnight,Add 200mL H2O,Extract three times with 90 mL of ethyl acetate,Combine ethyl acetate,Evaporation of ethyl acetate,Got a white solid.The residue was purified by silica gel column chromatography (petroleum ether: dichloromethane: ethyl acetate = 2: 1: 2)Yield 55%.

The synthetic route of 756520-66-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Southern Medical University; Wan Shanhe; Wang Guangfa; Wu Xiaoyun; Tian Yuanxin; Ye Ling; Li Zhonghuang; Zhang Tingting; Zhu Zhengguang; Jin Hong; Zhang Jiajie; (27 pag.)CN106565684; (2017); A;,
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Application of 172023-97-1, 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.172023-97-1, name is (3-Bromo-5-(trifluoromethyl)phenyl)methanol, molecular formula is C8H6BrF3O, molecular weight is 255.03, as common compound, the synthetic route is as follows.

[3-amino-5-(trifluoromethyl)phenyl]methanol (900 mg, 4.71 mmol) (Step A, Example 24) was suspended in CHBr3 (9 mL), and t-butyl nitrite (600 muL, 5.04 mmol) was added dropwise by syringe. The reaction was heated slowly to 80C and was maintained at this temperature for 10 minutes. The reaction was then cooled to room temperature, diluted with hexanes (50 mL), loaded on a silica gel column, and purified with 100% hexanes to 20% EtOAc/hexanes (2 columns) to afford [3-bromo-5- (trifluoromethyl) phenyl] methanol. Rf= 0.31 (25% EtOAc/hexanes). ‘H NMR (CDC13, 500 MHz) No. 7.71 (s, 1H), 7.68 (s, 1H), 7.56 (s, 1H), 4.76 (d, J = 5.5 Hz, 2H), 1.86 (t, J = 5.7 Hz, 1H). Step B: 3-Bromo-5-(trifluoromethyl)benzaldehyde A solution of [3-bromo-5-(trifluoromethyl)phenyl]methanol (409 mg, 1.61 mmol) in CH2Cl2 (25 mL) was cooled to 0C and then Dess-Martin periodinane (1.02 g, 2.41 mmol) was added. The reaction was stirred at 0 C for 30 minutes and then warmed to room temperature. After stirring at room temperature for thirty minutes, the reaction was poured into IN NaOH (25 mL). The mixture was extracted with EtOAc (100 mL), and the organic extracts were washed with IN NaOH (25 mL), then brine (25 mL), dried over Na2S04, filtered, and concentrated. Purification by flash chromatography with 25% EtOAc/hexanes afforded 3-bromo-5- (trifluoromethyl)benzaldehyde. 0.60 (25% EtOAc/hexanes). ‘H NMR (CDCI3, 500 MHz) 8 10.02 (s, 1H), 8.20 (s, 1H), 8.07 (s, 1H), 8.02 (s, 1H).

The chemical industry reduces the impact on the environment during synthesis 172023-97-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK & CO., INC.; WO2005/100298; (2005); A1;,
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Synthetic Route of 869725-53-1, 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. 869725-53-1, name is 2-Bromo-5-(trifluoromethyl)benzyl Alcohol, molecular formula is C8H6BrF3O, 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.

Preparation 3 1-Bromo-2-(bromomethyl)-4-(trifluoromethyl)benzene To a solution of (2-bromo-5-(trifluoromethyl)phenyl)methanol (4.7 g, 18 mmol) in methylene chloride (50 mL) at -10 C. was added carbon tetrabromide (CBr4) (7.17 g, 21.6 mmol). The resulting mixture was stirred at -10 C. for 15 minutes. Triphenylphosphine (5.61 g, 21.4 mmol) was then slowly added portionwise. This mixture was stirred at room temperature for 16 hours. The mixture was partitioned between saturated ammonium chloride (NH4Cl) (50 ml) and methylene chloride (2*50 mL). The combined organic layers were washed with saturated NaCl (50 mL), dried (MgSO4) and concentrated. The residue was purified by flash chromatography (silica gel) (eluted with 3:1 hexanes-ethyl acetate) to yield the title compound as a white solid (4.01 g). 1H NMR (400 MHz, CDCl3) delta 4.6 (s, 2H) 7.5 (dd, J=8.3, 1.6 Hz, 1H) 7.8 (m, 2H).

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 869725-53-1, 2-Bromo-5-(trifluoromethyl)benzyl Alcohol.

Reference:
Patent; Pfizer Inc; US2007/213371; (2007); A1;,
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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. 25574-11-2, name is 3-(4-Bromophenyl)propan-1-ol. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C9H11BrO

To a 0 C. mixture of 26A (7 g, 32.5 mmol) and NaHCO3 (3.28 g, 39.1 mmol) in DCM (200 mL) was added Dess-Martin periodinane (16.56 g, 39.1 mmol) and the reaction was allowed to slowly warm to rt overnight. The reaction was diluted with sat. aq. NaHCO3 (150 mL) and extracted with DCM (50 mL). The combined organic extracts were washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was chromatographed (SiO2; 80 g; A=Hex, B=EtOAc; 20 min gradient from 0% B to 40% B; flow rate=60 mL/min) to afford the title compound (4.06 g, 19.1 mmol, 58.5% yield) as a pale yellow oil. 1H NMR (500 MHz, CDCl3) delta 9.82 (t, J=1.2 Hz, 1H), 7.48-7.37 (m, 2H), 7.19-6.97 (m, 2H), 3.02-2.88 (m, 2H), 2.83-2.70 (m, 2H).

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, 25574-11-2, 3-(4-Bromophenyl)propan-1-ol.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; Shi, Yan; Cheng, Peter T.W.; Wang, Ying; Jusuf, Sutjano; Tao, Shiwei; Zhang, Hao; Wu, Shung C.; Robl, Jeffrey A.; (87 pag.)US2017/253554; (2017); 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.23783-42-8, name is 2,5,8,11-Tetraoxatridecan-13-ol, molecular formula is C9H20O5, molecular weight is 208.25, as common compound, the synthetic route is as follows.SDS of cas: 23783-42-8

A THF solution (200 mL) of H(OCH2CH2)4OMe (12 g, 60 mmol) and a stir bar was placed in a threenecked flask (500 mL). NaH (60%, dispersion in Paraffin Liquid, 2.9 g, 72 mmol) was added to the solution, and the mixture was stirred at room temperature for 30 min. Allyl bromide (6.2 mL, 72 mmol) was slowly added to the resulting mixture at the same temperature with vigorous stirring. The solution was stirred overnight, and the remaining NaH and NaBr were filtered off. The obtained filtrate was concentrated to dryness in vacuo. The residue was dissolved in water (500 mL) and extracted with hexane (200 mL3) and then dichloromethane (200 mL3). The resulting organic layer was dried with MgSO4 and then further dried under vacuum to afford the title compound 1d as a colorless oil (14 g, 55 mmol, 92%) 1d: 1H NMR (600 MHz, C6D6): delta 5.82 (m, CH2CHCH2O, 1H), 5.23 (m, CH2CHCH2O, 1H), 5.01 (m, CH2CHCH2O, 1H), 3.82 (m, CH2CHCH2O, 2H), 3.50-3.43 (m, CH2, 12H), 3.42-3.40 (m, CH2, 2H), 3.34 (m, CH2, 2H), 3.12 (s, OCH3, 3H). 13C{1H} NMR (150 MHz, C6D6): 135.7, 115.9, 72.4, 72.1, 71.07, 71.04 (3), 71.0, 70.9, 70.0, 58.6. HRMS (ESI): m/z calcd for [C12H24O5Na]+ (M+Na): 271.1516; found 271.1506.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,23783-42-8, 2,5,8,11-Tetraoxatridecan-13-ol, and friends who are interested can also refer to it.

Reference:
Article; Inomata, Koya; Naganawa, Yuki; Guo, Haiqing; Sato, Kazuhiko; Nakajima, Yumiko; Tetrahedron Letters; vol. 60; 41; (2019);,
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