Category: alcohols-buliding-blocks

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;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Reference of 637031-88-0, 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 637031-88-0, name is 3,3-Difluorocyclobutanol. This compound has unique chemical properties. The synthetic route is as follows.

[0433] Step D: Preparation of 6-fluoro-l-(trifluoromethyl)-5,6- dihvdrospirorcvclopentarc1pyridine-7,2′-rL31dioxolan1-4-ol and l-(trifluoromethyl)-5,6- dihvdrospirorcvclopentarc1pyridine-7,2′-rL31dioxolan1-4-ol: A solution of 4′-bromo-6′-fluoro- -(trifluoromethyl)spiro[l,3-dioxolane-2,7′-5,6-dihydrocyclopenta[c]pyridine] (96.2mg, 0.2800mmol) and 2-(di-t-butylphosphino)-3,6-dimethoxy-2′,4′,6′-tri-i-propyl-l, r-biphenyl (3.4 mg, 0.007 mmol) in 1,4-dioxane (5.0 mL) was sparged with nitrogen for 3 mins. The reaction mixture was then treated sequentially with potassium hydroxide (47.3 mg, 0.84 mmol), water (101 muEpsilon, 5.62 mmol) and [2-(2-aminophenyl)phenyl]-methylsulfonyloxy-palladium; di-t-butyl- [3,6-dimethoxy-2-(2,4,6-triisopropylphenyl)phenyl]phosphane (6.0 mg, 0.007 mmol) under continuous nitrogen stream. The vessel was sealed and heated to 80 C for 1 h and 30 min. The reaction mixture was quenched by the addition of acetic acid (64.3 muEpsilon, 1.13 mmol). The reaction mixture was poured into 75 mL of water and extracted with 4 x 20 mL EtOAc. The combined organics were dried with MgS04, filtered, and concentrated to dryness. The product was used without further purification (87 mg). During the reaction, some of the hydrodefluorinated product formed as an impurity. Data for 6-fluoro-l-(trifluoromethyl)-5,6- dihvdrospirorcvclopentarclpyridine-7.2′-ri.31dioxolanl-4-ol: LCMS ESI (+) (M+H) m/z 280. Data for l-(trifluoromethyl)-5,6-dihydrospiro[cyclopenta[clpyridine-7,2′-[L31dioxolanl-4-ol: LCMS ESI (+) (M+H) m/z 262. [0434] Step E: Preparation of 4-(3,3-difluorocvclobutoxy)-6-fluoro-l-(trifluoromethyl)- 5,6-dihydrospiro[cyclopenta[clpyridine-7,2′-[L31dioxolanel and 4-(3 , 3 -difluorocy clobutoxy)- 1 – (trifluoromethyl)-5,6-dihvdrospirorcvclopentarc1pyridine-7,2′-rL31dioxolane1: A solution of impure 6′-fluoro- -(trifluoromethyl)spiro[l,3-dioxolane-2,7′-5,6-dihydrocyclopenta[c]pyridine]- 4′-ol (44.0 mg, 0.16 mmol), polymer supported triphenylphosphine (-2.06 mmol/g, 306.2 mg, 0.63 mmol), and 3,3-difluoro-cyclobutanol (68.1 mg, 0.63 mmol) in tetrahydrofuran (3.2 mL) was treated with diisopropyl azodicarboxylate (120 mu^, 0.61 mmol) and stirred at 60 C for 2 h. The reaction mixture was filtered and the filter cake rinsed with 20 mL EtOAc. The filtrate was concentrated and purified by chromatography on silica using 10-30% EtOAc/hexane to afford a clear solid (39.0 mg, 67%) that was a 2: 1 mixture of the fluorinated and hydrodefluorinated products. LCMS ESI (+) (M+H) m/z 370. Data for 4-(3.3 -difluorocvclobutoxy)-6-fluoro- 1 – (trifluoromethyl)-5,6-dihvdrospirorcvclopentarc1pyridine-7,2′-rL31dioxolane1: LCMS ESI (+) (M+H) m/z 370. Data for 4-(3.3-difluorocvclobutoxyVl-(trifluoromethvn-5.6- dihvdrospirolcvclopentalc1pyridine-7.2′-r 1.3 ldioxolanel : LCMS ESI (+) (M+H) m/z 352.

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 637031-88-0, 3,3-Difluorocyclobutanol.

Reference:
Patent; PELOTON THERAPEUTICS, INC.; WEHN, Paul; XU, Rui; YANG, Hanbiao; (146 pag.)WO2016/144826; (2016); A1;,
Alcohol – Wikipedia,
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Related Products of 2919-23-5 ,Some common heterocyclic compound, 2919-23-5, molecular formula is C4H8O, 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 suspension of sodium hydride (2 equiv, 60% in mineral oil) in dry THF (0.44 M) under nitrogen atmosphere was added a solution of cyclobutanol (1.05 equiv) in dry THF (1.4 M) at 0 C. The reaction mixture was stirred at room temperature for 30 minutes before 2,4-dichloro-5-iodo-7-((2-(trimethylsilyl)ethoxy)-methyl)-7H-pyrrolo[2,3-d]pyrimidine (1 equiv) in dry THF (0.33 M) was added and the resulting reaction mixture was stirred at 30 C. for 1 h. The reaction mixture was quenched with saturated aqueous ammonium chloride solution. The organic solvent was removed under reduced pressure and the resulting aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was evaporated under reduced pressure. The crude obtained was purified by flash column chromatography on silica gel (5% ethyl acetate in petroleum ether) to afford the title compound (95% yield) as a white solid. MS (ESI) m/z 479.2 [M+1]+.

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. 2919-23-5, Cyclobutanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Signal Pharmaceutical LLC; Calabrese, Andrew Antony; Jeffy, Brandon; Robinson, Dale; Zhu, Dan; Huang, Dehua; Elsner, Jan; Boylan, John; Tehrani, Lida; Nagy, Mark A.; Moghaddam, Mehran Fallah; Raheja, Raj Kumar; Erdman, Paul; Narla, Rama K.; Harris, Roy L.; Tran, Tam Minh; Riggs, Jennifer; Ning, Yuhong; US2014/200206; (2014); A1;,
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Application of 2050-25-1, 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. 2050-25-1, name is 2-(2-(Benzyloxy)ethoxy)ethanol, molecular formula is C11H16O3, 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.

26.3 g of diethylene glycol benzyl ether was dissolved in 140 mL of DMF, 5.4 g of 60% NaH was added at 0 to 5 C., and the mixture was stirred for 30 minutes. Then, a solution of 17.3 g of 3-nitrophthalonitrile in 60 mL of DMF was added dropwise and the mixture was stirred at 0 to 5 C. for 2 hours. The reaction solution was discharged into 2500 mL of diluted hydrochloric acid, stirred for 30 minutes, and the precipitate was collected by filtration, washed with water and dried. The obtained solid was recrystallized from 80% isopropyl alcohol aqueous solution to obtain a yellowish white solid 21.7 g (melting point 98.5 to 100.5 C) was obtained.

According to the analysis of related databases, 2050-25-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; YAMAMOTO CHEMICALS INCORPORATED; KUMAGAE, YOJIRO; HORIUCHI, KENICHIRO; (40 pag.)JP2016/204536; (2016); A;,
Alcohol – Wikipedia,
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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. 1467-84-1, name is (trans-4-Aminocyclohexyl)methanol, the common compound, a new synthetic route is introduced below. category: alcohols-buliding-blocks

PREPARATION 50 2-((1r,4r)-4-Aminocyclohexyl)acetonitrile a) tert-Butyl (1 r,4r)-4-(hydroxymethyl)cyclohexylcarbamate Di-tert-butyl dicarbonate (3.04 g, 13.9 mmol) was added to a stirred solution of ((1r,4r)-4-aminocyclohexyl)methanol (1.50 g, 11.6 mmol) in tetrahydrofuran (20 mL). After stirring overnight at room temperature, the mixture was evaporated and partitioned between ethyl acetate and water. The organic layer was washed with water, brine, dried (MgSO4) and evaporated. The residue was treated with hexanes and the suspension was filtered to give the title compound (2.11 g, 79%) as a white solid. LRMS (m/z): 228 (M-H)+.1H NMR (300 MHz, DMSO-d6) delta ppm 0.84 – 0.95 (m, 2H), 1.05 – 1.18 (m, 2H), 1.20 – 1.29 (m, 2H), 1.40 (s, 9H), 1.71 -1.80 (m, 3H), 3.14 (m, 1H), 3.21 (t, 2H), 4.41 (t, 1H), 6.73 (d, 1H).

The synthetic route of 1467-84-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALMIRALL, S.A.; EASTWOOD, Paul Robert; GONZALEZ RODRIGUEZ, Jacob; GOMEZ CASTILLO, Elena; BACH TANA, Jordi; WO2011/157397; (2011); A1;,
Alcohol – Wikipedia,
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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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Synthetic Route of 100-37-8, 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 100-37-8 as follows.

Preparation of diethylaminoethyl 5-(2,4-difluorophenyl) salicylate.AcOH [39] 11.7 g (0.1 mol) of diethylaminoethanol was dissolved in 10% sodium bicarbonate (200 ml) and acetone (100 ml). 31.1 g (0.1 mol) of 5-(2,4-difluorophenyl) acetylsalicyl chloride was added into the reaction mixture. The mixture is stirred for 3 hours at RT. The solvents are evaporated off. The residue is suspended in ethyl acetate (500ml). 5% sodium bicarbonate (200 ml) is added into the reaction mixture with stirring. Ethyl acetate layer is collected and washed with water ( 3 x 500 ml). The ethyl acetate solution was dried over anhydrous sodium sulfate. Sodium sulfate is removed by filtration. 6 g of acetic acid is added into the reaction mixture with stirring. The organic solution was evaporated off. After drying, it yielded 36 g of the desired product (88%). Hygroscopic product; Solubility in water: 400 mg/ml; Elementary analysis: C H F NO5; MW: 409.42. Calculated % C: 61.60; H: 6.15; F: 9.28; N: 3.42; O: 19.54; Found % C: 61.56; H: 6.18; F: 9.27; N: 3.40; O: 19.59. 1H-NMR (400 MHz, CDCl3): delta: 1.56 (t, 6H), 2.21 (s, 3H), 3.27 (m, 4H), 3.70(m, 2H), 4.69 (t, 2H), 4.9 (b, IH), 6.74 (m, IH), 6.84 (m, IH), 7.0 (b, H), 7.06 (b, IH), 7.15 (m, IH), 7.44 (m, IH), 7.86 (m, IH).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,100-37-8, its application will become more common.

Reference:
Patent; TECHFIELDS BIOCHEM CO. LTD; YU, Chongxi; WO2008/12603; (2008); A1;,
Alcohol – Wikipedia,
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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. 3973-18-0, name is Propynol ethoxylate, molecular formula is C5H8O2, 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. Quality Control of Propynol ethoxylate

General procedure: 4-hydroxy-2-butanone (20, 1.00 g, 11.35 mmol) was pipetted into a dry flask and cooled to 0C under nitrogen atmosphere. 7N methanolic ammonia (11.2 mL, 79 mmol) was added via syringe, and the solution was allowed to stir at 0C for 3 hours. A solution of hydroxylamine-O-sulfonic acid (1.476 g, 13.05 mmol) in methanol (9.7 mL) was added dropwise, then was allowed to stir for an additional 16 hours while slowly warming to room temperature. The reaction was filtered through a sintered glass funnel, then transferred to a reaction vessel and re-cooled to 0C. Triethylamine (1.58 mL,11.35 mmol) was added, then molecular iodine (2.88 g, 11.35 mmol) was added slowly in 10 equal portions until the purple/brown color of iodine persisted in the reaction vessel. The solvent was removed under reduced pressure, and purification of the crude isolate via Kugelrohr distillation (60C, 1-3 torr) delivered the 2,2-diazirinyl intermediate as a clear oil (304 mg, 27% yield). A portion of this intermediate (300 mg, 3.00 mmol) was dissolved in dry pyridine (6 mL) and cooled to 0C in an ice bath. To this solution was added p-toluenesulfonyl chloride (628 mg, 3.30 mmol). The reaction mixture was allowed to stir for 24 hours at 0-4C, then was poured into a mixture of 37%w/v HCl (15 mL) and ice (80 mL). The resulting suspension was extracted 3x with ether, then the pooled organic layers were washed with 1N HCl solution, 1N NaOH solution, water, and brine. The organic extract was dried over MgSO4, vacuum filtered, and concentrated to a clear oil (428 mg, 15% yield over 3 steps) used without further purification. TLC Rf (2:1 hex:EtOAc) = 0.6. 1HNMR (500 MHz, CDCl3) delta 7.82 (d, J = 7.9 Hz, 2H), 7.37 (d, J= 7.9 Hz, 2H), 3.96 (t, J = 6.4 Hz, 2H), 2.46 (s, 3H), 1.68 (t, J= 6.4 Hz, 2H), 1.01 (s, 2H).

With the rapid development of chemical substances, we look forward to future research findings about 3973-18-0.

Reference:
Article; Yestrepsky, Bryan D.; Kretz, Colin A.; Xu, Yuanxi; Holmes, Autumn; Sun, Hongmin; Ginsburg, David; Larsen, Scott D.; Bioorganic and Medicinal Chemistry Letters; vol. 24; 6; (2014); p. 1538 – 1544;,
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Adding a certain compound to certain chemical reactions, such as: 6971-51-3, (3-Methoxyphenyl)methanol, 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, Product Details of 6971-51-3, blongs to alcohols-buliding-blocks compound. Product Details of 6971-51-3

A. m-Methoxybenzyl chloride To an ice cooled well stirred solution of 50 g. of m-methoxybenzyl alcohol in 500 ml. of benzene there are added, over the period of 20 minutes, 29 ml. of thionyl chloride in 40 ml. of benzene. At the end of an additional 30 minutes the ice bath was removed and the solution allowed to stand for 2 hours. Following this, the mixture was heated at reflux until the evolution of gas has ceased (30 minutes). The solvent was then removed in vacuum and the product distilled at 1.5 mm. There was obtained 39.94 g. of m-methoxybenzyl chloride, b.p. 63-69 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6971-51-3, (3-Methoxyphenyl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; The Upjohn Company; US3947520; (1976); A;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Reference of 15833-00-8 , The common heterocyclic compound, 15833-00-8, name is 2-(2-Aminophenyl)propan-2-ol, molecular formula is C9H13NO, 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.

112 g (1.13 mol) phosgene are piped into 500 mL THF. Then a solution of 52 g (0.34 mol) 2-(2-amino-phenyl)-propan-2-ol, prepared from 2-aminoacetophenone and methylmagnesium iodide, in 300 mL THF is added. The reaction mixture is left to stand overnight, concentrated by evaporation and combined with 500 ml of pyridine. After the pyridine has been distilled off the remainder is combined with water and extracted with diethyl ether. The organic phases are washed successively with 2 N hydrochloric acid, sodium hydroxide solution and water, dried with sodium sulphate and concentrated by evaporation. The residue remaining (46 g) is further reacted directly, without any more purification. M.p. (toluene/petroleum ether)=109-110 C.

The synthetic route of 15833-00-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boehringer Ingelheim International GmbH; US2007/37781; (2007); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts