Category: alcohols-buliding-blocks

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. 15852-73-0, name is (3-Bromophenyl)methanol, molecular formula is C7H7BrO, 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 C7H7BrO

Step 1 c’: Synthesis of (4′-(Trifluoromethyl)-[1 ,1 ‘-biphenyl]-3-yl)methanol To a solution of 3-bromo benzyl alcohol (0.1 g, 0.53 mM) and 4- (trifluoromethyl)phenyl)boronic acid (0.121 g, 0.64 mM), DMF/water (8:1 ), Na2C03 (0.142 g, 1 .33 mM) and PdCI2(PPh3)2 (0.010 mM) were added. The reaction mixture was heated in a microwave at 1 10 ¡ãC for 6 min. The reaction mixture was quenched with water and extracted with ethyl acetate (3×10 ml). The organic layer was washed with brine, dried over Na2S04 and concentrated to obtain a crude product, which was purified by column chromatography (silica gel, 100-200 mesh, eluted with 15percent ethyl acetate in petroleum ether) to afford the title compound (4’-(trifluoromethyl)-[1 ,1 ‘- biphenyl]-3-yl)methanol as a colorless oil. Yield: 0.108 g( 80percent);1H NMR (DMSO-d6, 300 MHz): delta 7.91 (d, J=8.1 Hz, 2 H), 7.84-7.82 (m, 3 H), 7.70 (m, 1 H), 7.50-7.48 (m, 2H), 5.30 (t, J = 5.7Hz, 1 H, OH), 4.60 (d, J=5.7 Hz, 2 H); MS: m/z 275 (M+Na).

With the rapid development of chemical substances, we look forward to future research findings about 15852-73-0.

Reference:
Patent; PIRAMAL ENTERPRISES LIMITED; KUMAR, Sanjay; SHARMA, Rajiv; MAHAJAN, Vishal, Ashok; SAWARGAVE, Sangameshwar, Prabhakar; WO2013/128378; (2013); A1;,
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Adding a certain compound to certain chemical reactions, such as: 111-46-6, 2,2′-Oxybis(ethan-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: 111-46-6, blongs to alcohols-buliding-blocks compound. Recommanded Product: 111-46-6

The preparation of this compound was adapted from a literature procedure. Into a suspension of tBuOK (5.10 g, 45.5 mmol) in dry THF (125 mL) was added die(thylene)glycol (9.55 g, 90.0 mmol) at 0 C under nitrogen atmosphere. The reaction mixture was allowed to stir at room temperature for 30 min then propargyl bromide (6.69 g, 45.0 mmol) in dry THF (25 mL) was added dropwise. The resulting mixture was allowed to stir at room temperature for 12 h. After completion of the reaction as indicated by NMR, the mixture was diluted with THF and filtered through Celite. The filtrate was concentrated and the residue was purified by column chromatography (Si02, EtOAc) to give the product as a pale yellow liquid (4.77 g, 93%). NMR (500 MHz, CDC13) delta 4.22 (d, J = 2.4, 2H, CH2C?C), 3.78 – 3.69 (m, 6Eta, CH2), 3.67 – 3.58 (m, 2Eta, CH2OH), 2.45 (t, J = 2.3, 2H, C?CH, OH). 13C NMR (126 MHz, CDC13) delta 79.6 (CH2C?CH), 74.8 (CH2C?CH), 72.6, 70.4, 69.3, 61.9 (CH2OH), 58.6 (CH2C?CH). The spectroscopic data of 39c are in agreement with those previously reported.

The synthetic route of 111-46-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PERCEC, Virgil; WO2014/190024; (2014); A1;,
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Adding a certain compound to certain chemical reactions, such as: 14320-38-8, Cyclopent-3-enol, 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, 14320-38-8, blongs to alcohols-buliding-blocks compound. Product Details of 14320-38-8

Step (i): l-[(cyclopent-3-en-l-yloxy)methyl]-4-methoxybenzene To a solution of cyclopent-3-en-l-ol (CAS number 14320-38-8; 15 g, 178 mmol) in dry THF (357 ml) at 0 C under nitrogen was added sodium hydride (60%, 9.27 g, 232 mmol). After fizzing had ceased, to this was then added dropwise l-(chloromethyl)-4- methoxybenzene (CAS number 824-94-2; 31.4 ml, 232 mmol). The reaction was then allowed to warm to room temperature for 17 hours. The reaction mixture was quenched by the addition of methanol and then concentrated in vacuo. The organics were partitioned between ethyl acetate and water. The organics were dried over magnesium sulfate, concentrated in vacuo and purified by column chromatography (silica, 0-50%dichloromethane / petrol) to afford the title compound.1H NMR (400 MHz, OCM-d2) delta ppm 2.33 – 2.47 (m, 2 H), 2.49 – 2.66 (m, 2 H), 3.79 (s, 3 H), 4.20 – 4.32 (m, 1 H), 4.40 (s, 2 H), 5.62 – 5.75 (m, 2 H), 6.86 (d, 7=8.59 Hz, 2 H), 7.24 (d, 7=8.59 Hz, 2 H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,14320-38-8, its application will become more common.

Reference:
Patent; TAKEDA CAMBRIDGE LIMITED; TAKEDA PHARMACEUTICAL COMPANY LIMITED; FIELDHOUSE, Charlotte; GLEN, Angela; ROBINSON, John Stephen; FUJIMOTO, Tatsuhiko; WO2015/55994; (2015); 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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Related Products of 50595-15-8, 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.50595-15-8, name is tert-Butyl 2-hydroxyacetate, molecular formula is C6H12O3, molecular weight is 132.16, as common compound, the synthetic route is as follows.

37.6 mg (0.285 mmol) of hydroxyacetic acid tert-butyl ester were dissolved in 10 ml of DMF, 12.4 mg of sodium hydride (55 percent in mineral oil) were added, and the mixture was stirred at room temperature for 15 min. Then 60 mg (0.237 mmol) of 3-bromo-6-(2-fluoro-phenyl)-pyridazine in 2 ml of DMF were added, and the reaction mixture was stirred at 60 ¡ãC for 5 h and at 120 ¡ãC for 5 h. After evaporation to dryness, the crude product was directly employed in the subsequent step.

Statistics shows that 50595-15-8 is playing an increasingly important role. we look forward to future research findings about tert-Butyl 2-hydroxyacetate.

Reference:
Patent; sanofi-aventis; EP1939181; (2008); 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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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. 4249-72-3, name is 2-Phenoxy-1-phenylethanol. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 2-Phenoxy-1-phenylethanol

0.2 mmol of lignin template compound,20mg catalyst,1.5mL of methanol was added to the 25mL inflation tube,After the oxygen was replaced three times, it was reacted in an oil bath at 80 to 120 C for 12 to 24 hours.After the reaction was cooled, the catalyst and the reaction liquid were separated, and the organic phase was evaporated to remove the solvent.The starting materials and yields are shown in the table below.

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, 4249-72-3, 2-Phenoxy-1-phenylethanol.

Reference:
Patent; Nanjing University of Science and Technology; Lu Guoping; Sun Kangkang; (6 pag.)CN108821952; (2018); A;,
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Reference of 1611-56-9 , The common heterocyclic compound, 1611-56-9, name is 11-Bromoundecan-1-ol, molecular formula is C11H23BrO, 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.

3,4-Dihydro-2H-pyran (21.87 g, 260 mmol) was added dropwise to a solution of 11-bromoundecanol (50.24 g, 200 mmol) and toluene-4-sulphonic acid monohydrate (80 mg, 0.4 mmol) in dichloromethane (100 ml). The reaction mixture was stirred at room temperature. After 24 h, the brown solution was filtered over a thin layer of silica gel. The filtrate was concentrated on the rotary evaporator and dried under fine vacuum. 65.85 g (196 mmol, 98% yield) of a light yellowish oil was obtained. 1H-NMR (CDCl3, 400 MHz): delta=1.23-1.37 (m, 12H), 1.37-1.47 (m, 2H), 1.48-1.64 (m, 6H), 1.65-1.76 (m, 1H), 1.77-1.90 (m, 3H), 3.35-3.42 (m, 3H), 3.46-3.53 (m, 1H), 3.70-3.75 (m, 1H), 3.84-3.90 (m, 1H), 4.56-4.58 (m, 1H). 13C-NMR (CDCl3, 100.6 MHz): delta=19.7, 25.4, 26.2, 28.2, 28.8, 29.4, 29.5, 29.6, 29.8, 30.8, 32.9, 33.9, 62.3, 67.7, 98.8.

The synthetic route of 1611-56-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IVOCLAR VIVADENT AG; Moszner, Norbert; Lamparth, Iris; Bock, Thorsten; Fischer, Urs Karl; Salz, Ulrich; Rheinberger, Volker; Liska, Robert; US2014/329929; (2014); 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.1877-77-6, name is 3-Aminobenzyl alcohol, molecular formula is C7H9NO, molecular weight is 123.15, as common compound, the synthetic route is as follows.Safety of 3-Aminobenzyl alcohol

General procedure: An oven-dried Schlenk tube (A) equipped with a magnetic stir bar was charged with AgF (132.2 mg, 1.05 mmol, 3.5 equiv), sealed with a septum, and degassed by alternating vacuum evacuation and nitrogen backfill (three times) before freshly distilled EtCN (3 mL)was added. To the resulting suspension, which was precooled to -78 C (dry ice-acetone bath), was added TMSCF3 (149.3 mg, 1.05 mmol, 3.5 equiv) by microsyringe. The mixture was allowed towarm to r.t. and stirring was continued for an additional 15 min. In due course, AgF solid dissolved and a gray, dark solution of [Ag-CF3] formed. Another Schlenk tube (B) equipped with a magnetic stir bar was charged with the aniline (ArNH2; 0.30 mmol, 1.0 equiv) in freshly distilled EtCN (1.5 mL). To the resulting solution, which was precooled to 0 C (ice bath), aq HCl (12 M; 50.0 muL, 0.60mmol, 2.0 equiv) was added; precipitate formed immediately. After 5 min stirring, t-BuONO (37.7 mg, 0.33 mmol, 1.1 equiv) was added by microsyringe, and the mixture was allowed to stir at 0 C for 15 min. The resulting suspension in Schlenk tube (B) was degassed by alternating vacuum evacuation at -196 C (liquid nitrogen), then the solution was allowed to warm to r.t. under a nitrogen atmosphere (three times), and finally cooled to -78 C (dry ice-acetone bath). The gray, dark solution of [AgCF3] in Schlenk tube (A), which was precooled to -78 C (dry ice-acetone bath), was added to Schlenk tube (B) (ArN2+Cl-) by syringe at -78 C (dry ice-acetone bath) over a period of 1 h. After the addition was complete, the reaction mixture was stirred for 3 h at -78 C (dry ice-acetone bath), allowed to warm to r.t., and stirring was continued for an additional 1 h. An off-white precipitate was observed, and the reaction mixture was diluted with EtOAc (3 mL) and filtered through a short silica gel column. The solvent was removed under reduced pressure with a rotatory evaporator, and the crude residue was purified by silica gel column chromatography to give the desired trifluoromethylation product 3. The yields of products 3a, 3f, 3g, 3l, 3o, 3r, 3x, and 3zb are based on the 19F NMR spectra with 4-F3COC6H4OMe as internal standard. Analytical data for the representative product ethyl 4-(trifluoromethyl)benzoate (3i) are provided below. Data for other products can be found in the literature.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1877-77-6, 3-Aminobenzyl alcohol, and friends who are interested can also refer to it.

Reference:
Article; Wang, Xi; Xu, Yan; Zhou, Yujing; Zhang, Yan; Wang, Jianbo; Synthesis; vol. 46; 16; (2014); p. 2143 – 2148;,
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