Tag: M.W=200-300

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.162021-14-9, name is (2-Amino-9H-fluoren-9-yl)methanol, molecular formula is C14H13NO, molecular weight is 211.26, as common compound, the synthetic route is as follows.HPLC of Formula: C14H13NO

Example 4 Synthesis of tert-Butyldimethylsiloxy-9-methyl-2-aminofluorene 5.91 g Imidazole (86.8 mmol, 2.1 equiv) was dissolved in 24 ml dry DMF and stirred 10 min in an iced bath under argon atmosphere. 7.47 g tertButyldimethylsilyl chloride (49.6 mmol, 1.2 equiv) dissolved in dry DMF was added. After 15 min stirring on ice 8.73 g 9-Hydroxymethyl-2-amino fluorene (41.3 mmol) dissolved in 40 ml dry DMF was added drop wise under cooling and argon atmosphere. The reaction was continued 15 min on ice and then at room temperature. The reaction was monitored by TLC [title product Rf=0.6, PE-MTBE (1:2)]. After 2 hours the starting product [Rf=0.1 PE-MTBE (1:2)] had disappeared and the reaction mixture was diluted with 400 ml CH2Cl2 and 100 ml 5% NaHCO3 was added. The organic phase was washed with 5*200 ml H2O and dried over Na2SO4. CH2Cl2 was eliminated by rotary evaporation and DMF was eliminated by azeotropic distillation with toluene. The residual brown oil (13.4 g, 99% yield) was analyzed by NMR and was used without further purification. 1H NMR (200 MHz/DMSO) delta=7.67-7.40 (3H; m; 3*Ar-H); 7.34-7.00 (2H; m; 2*Ar-H); 6.81 (1H; s; 1*Ar-H); 6.59 (1*; dd; J=8.02 Hz & 1.83 Hz; 1*Ar-H); 5.19 (2H; s; NH2); 3.97-3.76 (2H; m; CH2); 3.75-3.57 (1H; m; CH); 0.88 (9H; s; 3*CH3); 0.03 (6H; s; 2*CH3) 13C NMR (50 MHz/DMSO) delta=148.40 (Ar-Cqu); 145.81 (Ar-Cqu); 143.67 (Ar-Cqu); 141.88 (Ar-Cqu); 129.08 (Ar-Cqu); 127.10 (Ar-CH); 124.97 (Ar-CH); 124.16 (Ar-CH); 120.47 (Ar-CH); 117.87 (Ar-CH); 113.22 (Ar-CH); 110.58 (Ar-CH); 66.04 (CH2-OH); 49.60 (C9); 25.88 (3*CH3; t-Bu); 18.04 (Cqu; t-Bu), -5.04 (2CH3; Si-CH3)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,162021-14-9, (2-Amino-9H-fluoren-9-yl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; Baxter International Inc.; Baxter Healthcare SA; US2009/5574; (2009); 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.575-03-1, name is 7-Hydroxy-4-(trifluoromethyl)coumarin, molecular formula is C10H5F3O3, molecular weight is 230.1401, as common compound, the synthetic route is as follows.Recommanded Product: 7-Hydroxy-4-(trifluoromethyl)coumarin

The synthetic steps of 4-trifluoromethyl-7-propylenecarbonyloxycoumarin are as follows:(1) To 10 mL of a solution containing 0.5 mmol of 4-trifluoromethyl-7-hydroxycoumarin and 0.625 mmol of triethylamine in a tetrahydrofuran solution, slowly add 0.6 mmol of acryloyl chloride chloride to the reaction flask within 30 min. Dissolved in 5 mL of tetrahydrofuran), the temperature is controlled at 0 ° C;(2) After stirring for 1 hour under ice bath conditions, the temperature of the solution was raised to room temperature and stirred overnight. ;(3) The reaction solution was subjected to a solvent under reduced pressure, and the residue was purified by silica gel chromatography eluting with ethyl acetate-hexane (1:3 v/v)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,575-03-1, 7-Hydroxy-4-(trifluoromethyl)coumarin, and friends who are interested can also refer to it.

Reference:
Patent; Da Lianli Technology Changshu Institute Co., Ltd.; Cui Jingnan; Feng Lei; (12 pag.)CN103755672; (2016); B;,
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Synthetic Route of 722-92-9, 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 722-92-9, name is 2-(4-Aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: The compound 1(4-(chloromethyl)benzoyl chloride, 12 mmol) was added dropwise to a mixture of 2a?n (10 mmol) and triethylamine (12 mmol) in dichloromethane (20 mL) at room temperature with stirring. Then the reaction mixture was refluxed for 4?6 h. After cooling to room temperature, the mixture was slowly poured to ice water (50 mL). The solution was extracted with dichloromethane (3×60 mL) and the organic phase was dried over with sodium sulfate anhydrous. After removal of the dichloromethane, the solid residue was purified by recrystallization with petroleum ether?ethyl acetate to give compounds 3a?n.

According to the analysis of related databases, 722-92-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Shi, Yao-Jie; Song, Xue-Jiao; Li, Xiao; Ye, Ting-Hong; Xiong, Ying; Yu, Luo-Ting; Chemical and Pharmaceutical Bulletin; vol. 61; 11; (2013); p. 1099 – 1104;,
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Related Products of 575-03-1, 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 575-03-1, name is 7-Hydroxy-4-(trifluoromethyl)coumarin. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: The appropriate bromoketone (6a-o) (1.7 mmol) and triethylamine (1.6 mmol) were added to as olution of either7-hydroxy-4-methyl-2H-chromen-2-one 4 (1.4 mmol)or 7-hydroxy-4-(trifluoromethyl)-2H-chromen-2-one 5 (1.4 mmol) in THF (20 mL). The mixture was stirred at room temperature for 24h, filtered and the solvent was evaporated under reduced pressure.The solid residue was purified by column chromatography eluting with DCM/MeOH 9:1 to afford (7a-n) and (8a-o).

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 575-03-1, 7-Hydroxy-4-(trifluoromethyl)coumarin.

Reference:
Article; Kandil, Sahar; Westwell, Andrew D.; Mcguigan, Christopher; Bioorganic and Medicinal Chemistry Letters; vol. 26; 8; (2016); p. 2000 – 2004;,
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Electric Literature of 149104-89-2, Adding some certain compound to certain chemical reactions, such as: 149104-89-2, name is (4-Bromo-3-methylphenyl)methanol,molecular formula is C8H9BrO, 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 149104-89-2.

9.10 g of (4-bromo-3-methylphenyl)methanol was dissolved in 91 ML of methylene chloride and cooled to 5°C, to which 19.7 ML of N-ethyldiisopropylamine and 6.9 ML of chloromethyl methyl ether were successively added dropwise at 5 to 10°C, and then this mixture was stirred for 2.5 hours at room temperature.. water was added to the reaction mixture and adjusted to PH 7 with 6M hydrochloric acid, and then the organic phase was separated therefrom.. After the resultant organic phase was washed with water and a saturated sodium chloride solution successively, the washed phase was dried over anhydrous sodium sulfate, and the solvent was distilled out under reduced pressure.. The resultant residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=5:1] to yield 10.44 g of 1-bromo-4-[(methoxymethoxy)methyl]-2-methylbenzene as yellow oil. NMR(400MHz,CDCl3) delta value: 2.40(3H,s), 3.41(3H,s), 4.52(2H,s), 4.71(2H,s), 7.04(1H,dd,J=8.2,2.0Hz), 7.23(1H,d,J=1.6Hz), 7.50(1H,d,J=8.0Hz)

According to the analysis of related databases, 149104-89-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TOYAMA CHEMICAL CO., LTD.; Hirono, Shuichi; Shiozawa, Shunichi; EP1445249; (2004); A1;,
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Adding a certain compound to certain chemical reactions, such as: 143726-85-6, tert-Butyl 4-(hydroxymethyl)benzoate, 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: 143726-85-6, blongs to alcohols-buliding-blocks compound. Recommanded Product: 143726-85-6

alpha-[4-Chlorobenzenesulfonylamino]-3,5- difluorobenzeneacetamide (300 mg, 0.83 mmol) was dissolved in dry THF (2.5 mL) and the resulting solution was cooled to 0 0C with stirring under a nitrogen atmosphere. Diisopropylazodicarboxylate (420 mg, 409 muL, 2.08 mmol) was added and the reaction mixture was stirred for 15 min. t-Butyl 4-hydroxymethylbenzoate (433 mg, 2.08 mmol) was dissolved in dry THF (2.5 mL) and the resulting solution was cooled to 00C with stirring under a nitrogen atmosphere. Triphenylphosphine (545 mg, 2.08 mmol) was added and the reaction mixture was stirred for 15 min. The solution containing the alcohol was added to the other solution in one portion. The reaction mixture was warmed to ambient temperature over 18h; then it was diluted with EtOAc (50 mL). The organic solution was washed with water (15 mL) four times and with brine (20 mL) twice. Drying over MgSO4, filtration and concentration of the filtrate in vacuo gave crude product. Column chromatography was performed twice (EtOAc:hexane:: 1:4, then 1 :3 (twice)). The crude product was then triturated six times with a mixture of hexane-ether-MeOH (8: 1 : 1). Drying in vacuo afforded the title product (white solid, 207 mg, 45% yield): 1H NMR (MeOH- d4, 300 MHz): 7.81 (d, 2H, J = 8), 7.65 (d, 2H, J = 8), 7.55 (d, 2H, J = 8), 7.10 (d, 2H, J = 8), 6.85 (d, 2H, J = 8), 6.76 (t, IH, J = 8), 5.82 (s, IH), 4.83 (m, 4H), 1.57(s, 9H); HRMS (ES+): Calcd for C26H29ClF2N3O5S (M+ + NH4): 568.1485, Found: 568.1475.

The synthetic route of 143726-85-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2009/137657; (2009); A1;,
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Related Products of 149965-40-2, 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. 149965-40-2, name is (5-Bromo-2-chlorophenyl)methanol, molecular formula is C7H6BrClO, 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.

60 g PCC and 60 g silica gel powder were added to a round bottom flask; after mixing, 500 mL dichloromethane was added; cooled to 0 C., and 45 g of compound 1-1 in dichloromethane (300 mL) was added dropwise with stirring; maintaining 0 C.The reaction was monitored by TLC; after the reaction was completed, the reaction solution was spin-dried; 38 g of Compound 1-2 was isolated by column separation, and the yield in two steps was 90%.

According to the analysis of related databases, 149965-40-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Guangzhou Medical University; Hu Wenhui; Yu Xiyong; Zhao Xin; Wu Bo; (25 pag.)CN107556276; (2018); A;,
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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, 106-28-5, blongs to alcohols-buliding-blocks compound. Computed Properties of C15H26O

Farnesol (10) (2.0 mL, 8 mmol) was dissolved in anhydrous DMF (80 mL) and cooled to 0 C. Collidine (6.3 mL, 48 mmol) and MsCl (1.3 mL, 16 mmol) were added to the mixture. After stirring at 0 C for 15 min, anhydrous LiCl (1.35 g, 32 mmol) was added. The reaction was stirred at 0 C for 3 h. H2O (80 mL) was added and the mixture was extracted with hexane (50 mL 3). The combined organic phases were washed with CuSO4 (sat.), NaHCO3 (sat.) and brine. The resulting solution was dried over anhydrous Na2SO4 and concentrated under reduced pressure. Compound 11 was obtained as a yellow oil and used in the next step without purification.1H NMR (300 MHz, CDCl3): d (ppm) 5.46 (1H, t, J = 8.0), 5.12-5.08 (2H, m), 4.12 (2H, d, J = 8.0), 2.23-1.98 (8H, m), 1.73 (3H, s),1.66 (3H, s), 1.61 (6H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,106-28-5, its application will become more common.

Reference:
Article; Tang, Xiaoping; Demiray, Melodi; Wirth, Thomas; Allemann, Rudolf K.; Bioorganic and Medicinal Chemistry; vol. 26; 7; (2018); p. 1314 – 1319;,
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Reference of 83647-43-2 , The common heterocyclic compound, 83647-43-2, name is (3-Bromo-2-methylphenyl)methanol, molecular formula is C8H9BrO, 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.

To a fiask charged with (3-bromo-2- methylphenyl)methanol (6.0 g, 30 mmol) was added a lM TFA solution of thallium trifluoroacetate (16.2 g, 29.8 mmol). The mixture was stirred at RT oyernight. Analysis by TLC showed no starting material remaining. The solyent was remoyed under yacuum, and the residuewas pumped under high yacuum for 30 min to ensure complete remoyal of TFA. To the residue was then added palladium(II) chloride (529 mg, 2.98 mmol), lithium chloride (2.53 g, 59.7 mmol), magnesium oxide (2.41 g, 59.7 mmol), and MeOH (150 mL). The reaction was flushed with CO twice, and kept under CO at room temperature. Analysis by LC showed a big product spot within 2 hours. To this solution was added ethyl acetate to precipitate the salts. The blaeksolution was filtered through a CELITE pad, washed with EtOAc, adsorbed onto silica and purified by silica gel chromatography to afford title compound. 1H-NMR (500 MHz, CDC13)ppm 7.71 (d, J= 8.0 Hz, 1H), 7.58 (d, J= 8.0 Hz, 1H), 5.25 (s, 2H), 2.37 (s, 3H).

The synthetic route of 83647-43-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; PASTERNAK, Alexander; DE JESUS, Reynalda, Keh; DING, Fa-xiang; DONG, Shuzhi; FRIE, Jessica; GU, Xin; JIANG, Jinlong; SHAHRIPOUR, Aurash; PIO, Barbara; TANG, Haifeng; WALSH, Shawn; WO2014/126944; (2014); A2;,
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Related Products 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.

To a round bottom flask was added (4-bromo-3,5-dimethoxy-phenyl)methanol (Compound 10, 0.5 g, 2.02 mmol) and dichloromethane (15 mL). The reaction was cooled to 0 °C and diethylaminosulfur trifluoride (0.360 g, 2.23 mmol) was added. The reaction was allowed to warm to room temperature and stir for 1 hour. The reaction was quenched using saturated sodium bicarbonate, the layers were separated and the organic layer was dried using sodium sulfate, filtered and concentrated in vacuo. The resulting solid was purified on silica gel using ethyl acetate and hexanes as eluent. Product, 2-bromo-5-(fluoromethyl)-l,3- dimethoxybenzene, (Compound 14, 0.171 g, 33.9percent yield) was isolated as a pale yellow solid. LC-MS: tR=2.23 min; m+H=249.0, 251.0 (bromine isotopes).

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; SAINT LOUIS UNIVERSITY; WASHINGTON UNIVERSITY; RUMINSKI, Peter, G.; MEYERS, Marvin, L.; HEIER, Richard, F.; RETTIG, Michael, P.; DIPERSIO, John; (139 pag.)WO2018/85552; (2018); A1;,
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