Author: Jessica.F

These common heterocyclic compound, 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, 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. 54314-84-0

To a solution of Lambda/-[4-(7-Hydroxy-6-methoxy-quinoIin-4-yloxy)-phenyl]-benzamide (0.12g, 0.32mmol) in DMF (3ml) was added potassium carbonate (0.11g, O.deltammol, 2.5eq) and benzyl 3- bromopropyl ether (64ul, 0.36mmol, 1.1 eq). The reaction wasstirred at room temperature for 48 hours. The DMF was removed under reduced pressure and ethyl acetate was added to the crude residue, washing with water. The ethyl acetate layer was dried over magnesium sulphate and evaporated under reduced pressure. The product was purified by column chromatography, eluting with ethyl acetate/heptane (2:1 ) to yield the title compound (0.15g, 90percent) as a yellow solid, m/z 535 [M+H]+.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 54314-84-0.

Reference:
Patent; CHROMA THERAPEUTICS LTD; WO2006/117570; (2006); A1;,
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Some common heterocyclic compound, 454-90-0, name is 3-(Trifluoromethyl)anisole, molecular formula is C8H7F3O, 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. 454-90-0

1. Preparation of 2-Propylthio-3-(trifluoromethyl)-anisole A solution of 30 mL (milliliter) (208 mmol) (millimole) of 3-(trifluoromethyl)anisole in 500 mL of dry tetrahydrofuran was cooled to -70 C. under a nitrogen blanket and 100 mL (250 mmol) of 2.5M butyl lithium in hexane was added slowly with stirring and cooling. The reddish solution was stirred at -70 C. for 1 hour and then 42 mL (270 mmol) of dipropyl disulfide was added slowly with stirring and cooling. The resulting mixture was allowed to warm to ambient temperature over an 18-hour period. The mixture was quenched with 250 mL of saturated aqueous ammonium chloride. The organic phase was recovered, dried over magnesium sulfate, and concentrated by evaporation under reduced pressure. The yellow oil residue was fractionally distilled in a Vigreux column at 0.2 mm Hg (millimeters of mercury) (27 Pascals) to obtain 37 g (gram) (71 percent of theory) of a clear liquid product fraction boiling at 92 C.

The chemical industry reduces the impact on the environment during synthesis 3-(Trifluoromethyl)anisole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Dow AgroSciences LLC; US5858924; (1999); A;,
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1535-75-7, 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. 1535-75-7, name is 2-(Trifluoromethoxy)aniline, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Pd(OAc)2 (20 mg, 0.09 mmol), (+/-)-BINAP (55 mg, 0.09 mmol), and DMF (5 mL) were charged in a round-bottom flask flushed with argon. The flask was evacuated and backfilled with argon. The mixture was stirred under argon for 30 min and added to a mixture of 27 (345 mg, 0.9 mmol), 2-trifluoromethoxyaniline (0.184 mL, 1.35 mmol), and K2CO3 (1.24 g, 8.97 mmol) in DMF (10 mL). The resulting mixture was stirred at 80 C for 4 h under argon. After cooling to room temperature, the reaction mixture was filtered on a pad of celite. The solvent was evaporated, the crude solid was purified by flash chromatography on silica gel (eluant: DCM/EtOH 90/10) to afford 210 mg (54%) of 31 as white solid.

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.

Reference:
Article; Caldarelli, Marina; Angiolini, Mauro; Disingrini, Teresa; Donati, Daniele; Guanci, Marco; Nuvoloni, Stefano; Posteri, Helena; Quartieri, Francesca; Silvagni, Marco; Colombo, Riccardo; Bioorganic and Medicinal Chemistry Letters; vol. 21; 15; (2011); p. 4507 – 4511;,
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The chemical industry reduces the impact on the environment during synthesis 402-52-8, name is 1-Methoxy-4-(trifluoromethyl)benzene, I believe this compound will play a more active role in future production and life. 402-52-8

To chloro sulfuric acid (15 mL) was added l-methoxy-4-trifluoromethyl- benzene (3.0 g, 17 mmol) portionwise at 0C. The mixture was stirred at room temperature overnight. The mixture was poured into ice. the aqueous layer was extracted with EtOAc (50 mL x3). The extracts were dried over Na2S04 and the solution was filtered through a pad of silica gel, dried in vacuum to afford 500 mg (yield: 11%) of 2-methoxy-5-trifluoromethyl- benzenesulfonyl chloride as white solid. [00183] 1H NMR (DMSO-d6): delta = 7.90 (1H, d), 7.67 (1H, dd), 7.18 (1H, d), 3.84 (3H, s).

The chemical industry reduces the impact on the environment during synthesis 402-52-8. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SANFORD-BURNHAM MEDICAL RESEARCH INSTITUTE; PINKERTON, Anthony, B.; DAHL, Russell; COSFORD, Nicholas, D.P.; MILLAN, Jose, Luis; WO2013/126608; (2013); A1;,
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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. 4344-55-2 name is 4-Butoxyaniline, This 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. 4344-55-2

1-bromonaphthalene: 22.78 g (110 mmol) 4-butoxyaniline: 8.26 g, 50 mmol Pd2 (dba)3: 1.007 g, 1.1 mmol P(t-Bu)3: 0.89 g (8.9 g in 10% hexane solution), 4.4 mmol tBuONa: 14.8 g, 154 mmol To a three-necked flask equipped with a reflux condenser, 1-bromonaphthalene, 4-butoxyaniline, Pd2 (dba)3, P(t-Bu)3, t-BuONa and toluene (150 ml) are added and stirred at 80 C. until the 4-butoxyaniline disappears as shown by HPLC analysis. After the reaction is completed, the reaction mixture is passed through a column packed with 6 inches of neutral alumina, and 2 L of toluene eluent is collected. The solvent is removed on rotary evaporator. The residue is extracted with 250 ml of diethyl ether, and the organic layer is washed with 3¡Á200 ml of brine. The organic layer is dried over MgSO4 and concentrated on a rotary evaporator. The crude product is recrystallized from isopropanol. The final product is an off-white powder with a purity of 98.5% as determined by HPLC; the yield is 54%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Butoxyaniline, and friends who are interested can also refer to it.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; US2012/264977; (2012); A1;,
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134364-69-5, 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. 134364-69-5, name is 2,3-Difluoroanisole, This compound has unique chemical properties. The synthetic route is as follows.

To a mixture of l,2-difluoro-3-methoxybenzene (3.0 g, 21 mmol) in anhydrous tetrahydrofuran (40 mL) at -70 C under nitrogen was added dropwise tert-butyllithium (19 mL, 25 mmol, 1.3 M in n-pentane). The mixture was stirred at this temperature for 30 minutes, then NN- dimethylformamide (6.1 g, 83 mmol) was added dropwise at -70 C. The reaction was stirred at – 70 C for another 2 hours. On completion, the mixture was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo to give compound B-168 (4.0 g, crude) as a yellow solid. LCMS (B): tR=0.661 min., (ES+) m/z (M+H)+ =173.1.

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.

Reference:
Patent; FORUM PHARMACEUTICALS, INC.; ACHARYA, Raksha; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; COOK, Andrew, Simon; HARRISON, Bryce, Alden; KOENIG, Gerhard; MCRINER, Andrew, J.; (400 pag.)WO2016/100184; (2016); A1;,
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7025-06-1, The chemical industry reduces the impact on the environment during synthesis 7025-06-1, name is 1-Bromo-2-phenoxybenzene, I believe this compound will play a more active role in future production and life.

General procedure: Toasolutionofbromide12(a-c)(0.3mmol)and bis(triphenylphosphine)palladium(II)dichloride(9mumol),N-ethyl-N-isopropylpropan-2-amine(0.3mmol)andcopper(I)iodide(0.03mmol)inDMF(1.5ml)wasaddedtheappropriatealkynerelatedalkyne(0.45mmol)andthevesselwasflushedwithargon,sealedandheated(70¡ãC,overnight).Theresultingdarkmixturewascooledtoroomtemperatureandpurifiedbysilicagelchromatographytoafford13(a-d).

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-2-phenoxybenzene. I believe this compound will play a more active role in future production and life.

Reference:
Article; Zhao, Xue Zhi; Hymel, David; Burke, Terrence R.; Bioorganic and Medicinal Chemistry Letters; vol. 26; 20; (2016); p. 5009 – 5012;,
Ether – Wikipedia,
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402-07-3, 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 402-07-3 as follows.

To a solution of 1-bromo-2-methoxy-4-(trifluoromethyl)benzene (69.0 mg, 0.27 mmol) in dry THF (4 mL) at -78 C under N2 was slowly added N-BuLi (0.11 mL, 2.5 M in N-pentane, 0.27 mmol). After being stirred for 30 min, a solution of 8 (50 mg, 0.11 mmol) in dry THF (1 mL) was added slowly via a syringe. The mixture was stirred for about 2 h and quenched by addition of a saturated aqueous NH4Cl (15 mL) solution, and extracted with EtOAc (10 mL ¡Á 3). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated in vacuum. The residue was purified by flash column chromatography (15% EtOAc/petroleum ether, Rf = 0.2) to give 25 (56 mg, 81%) as a pale brown solid. mp 34.7-36.7 C; 1H NMR (400 MHz, CDCl3) delta 0.001 (s, 3H), 0.07 (s, 3H), 0.83 (s, 9H), 2.41 (s, 3H), 2.94 (d, J = 4.0 Hz, 1H), 3.73 (s, 3H), 4.43 (d, J = 12.0 Hz, 1H), 4.75 (d, J = 12.0 Hz, 1H), 5.81-5.84 (m, 2H), 6.10 (t, J = 3.2 Hz, 1H), 6.34 (d, J = 3.6 Hz, 1H), 6.66 (dd, J = 3.6, 2.0 Hz, 1H), 6.99 (s, 1H), 7.18 (d, J = 8.0 Hz, 1H), 7.24 (d, J = 3.6 Hz, 1H), 7.30 (d, J = 8.0 Hz, 2H), 7.55 (d, J = 8.0 Hz, 1H), 7.85 (d, J = 8.4 Hz, 2H) ppm; 13C NMR (CDCl3, 100 MHz) delta -5.71, -5.67, 18.53, 21.56, 25.92, 25.92, 25.92, 53.27, 55.53, 62.79, 106.87, 106.91, 108.05, 108.43, 111.37, 117.21, 117.25, 121.56, 123.91, 126.96, 127.01, 127.35, 128.40, 129.44, 129.87, 134.75, 134.76, 135.81, 136.29, 145.17, 156.02 ppm; HRMS (M + Na+) calcd. for C31H37F3N2NaO5SSi 657.2042, found 657.2040; IR (KBr) 3383, 3146, 2956, 2929, 2857, 1734, 1594, 1465, 1415, 1377, 1329, 1241, 1175, 1123, 1032, 841, 778, 670 cm-1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 402-07-3, and friends who are interested can also refer to it.

Reference:
Article; Cheng, Chunwei; Liu, Yan; Song, Hao; Pan, Lili; Li, Jerry; Qin, Yong; Li, Rongshi; Marine Drugs; vol. 11; 8; (2013); p. 2927 – 2948;,
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Adding a certain compound to certain chemical reactions, such as: 349-55-3, name is 3-Methoxy-5-(trifluoromethyl)aniline, belongs to ethers-buliding-blocks compound, 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 349-55-3, 349-55-3

EXAMPLE 124 4-(3-Methoxy-5-trifluoromethylanilino)-2-(3-pyridinyl)-6-(trifluoromethyl)pyrimidine The title compound was prepared from a mixture of 4-chloro-2-(3-pyridinyl)-6-(trifluoromethyl)pyrimidine (50 mg, 0.193 mmol) and 3-methoxy-5-trifluoromethylaniline (55 mg, 0.290 mmol) similar to Example 117 and isolated as a yellow solid (27 mg, 34%). 1H NMR (CDCl3): 9.65-9.64 (m, 1H), 8.75-8.70 (m, 2H), 7.46-7.41 (m, 2H), 7.36 (s, 1H), 7.31 (s, 1H), 7.00 (s, 1H), 6.93 (s, 1H), 3.91 (s, 3H).

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, 3-Methoxy-5-(trifluoromethyl)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Cytovia, Inc.; US2003/69239; (2003); A1;,
Ether – Wikipedia,
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101-84-8, The chemical industry reduces the impact on the environment during synthesis 101-84-8, name is Diphenyl oxide, I believe this compound will play a more active role in future production and life.

Example 1; Decabromodiphenyl ether – Simultaneous bromination and milling in a mixed solvent; To a 1 liter round bottomed flask equipped with a mechanical stirrer, a dropping funnel, a thermocouple and a reflux condenser was added 440 g of solvent mixture (DCM 20 %, CBM 40 %, and DBM 40 % w/w) ; bromine, 475 g; AlCl3,4.3 g; and ceramic beads (1.5-3.5 mm diameter), 814 g-A solution of diphenyl oxide (42.5 g, ) in 20 ml of solvent mixture was dropped into the flask during 70 minutes with stirring while keeping the temperature at 7- 13 C . The reaction mixture was refluxed for 4.5 hours, the flask was cooled and 55 ml of water was carefully added to destroy the catalyst. Excess bromine was bleached with sodium bisulfite solution, the aqueous phase was separated and the organic phase was washed with water. The product mixture was passed through a sieve to remove the ceramic beads and the mixture was filtered, washed with water and dried. The product comprised 99.4 % decabromodiphenyl ether and 0.1 % nonabromodiphenyl ether (in the Examples sometimes abbreviated “Deca” and “Nona”, respectively). Particle size 7.1 microns (dg0) .; Example 2 (comparative); Decabromodiphenyl ether – Bromination without milling in a mixed solvent.; The procedure of Experiment 1 was repeated without the ceramic beads present. The product consisted of 94.1 % Deca and 5.8 % Nona. Particle size 98 microns (d90).; Example 3; Decabromodiphenyl ether- increasing the crystal size of milled Deca in a simulated reaction mixture after bromination and destruction of the catalyst.; The product of Example 1, having a particle size of 7.1 microns (dgo) and an assay of 99.4 %, was charged to a 1 liter flask followed by 440 g of solvent mixture (DCM 20 %, CBM 40 %, and DBM 40 %); 4.3 g AlCl3, 50 g of bromine and 50 ml of water to destroy the catalyst. The mixture was refluxed for 5.3 hours, cooled and bleached with bisulfite. The product was filtered, washed with water and dried. The particle size v/as 28.8 microns (dgo), had an assay of 99.7 % and was easily filtered.; Example 7; Decabromodiphenyl ether – Bromination of pre-milled Deca precursor; To a 2 liter jacketed reaction vessel equipped with a mechanical stirrer, a dropping funnel, a thermocouple and a reflux condenser was added 500 g of milled Deca (content 97.3 %, particle size 3.8 microns (d90) ) , 1945 g of solvent mixture, 444 g bromine and 22 g AICI3. The mixture was heated at reflux for 3.5 hours. Water, 260 ml, was added and the excess bromine was bleached with sodium bisulfite solution. To the thick slurry was added 150 ml of water. The mixture was filtered and the dried solid comprised 99.6 % Deca with particle size 38.5 microns (dgo).; Example 8; Decabromodiphenyl ether- Bromination of pre-milled Deca precursor on an industrial scale; A reactor vessel of 16 cubic meters capacity was charged with 7500 liters of solvent consisting of 12.6 % dichloromethane, 32.5 % bromochloromethane and 54.9 % dibromomethane . Aluminum chloride, 150 kg, 8 tons of pre- milled Deca (Deca content 97.9 % with particle size 14 microns (dg0) ) and 1000 kg of bromine were added. The mixture was heated at reflux for 8 hours and was then bleached with 1340 liters of 38 % sodium bisulfite solution. The upper aqueous solution was decanted and the mixture was washed with two 1200 liters portions of water. Sodium hydroxide, 20 %, was added to neutralize the mixture which was then centrifuged. The product was dried and was found to contain 99.3 % Deca with particle size 42 microns (d90).; Example 9; Decabromodiphenyl ethane – Simultaneous bromination and milling in a mixed solvent; To a 1 liter round bottomed flask equipped with a mechanical stirrer, a dropping funnel, a thermocouple and a reflux condenser was added 520 g of solvent mixture (DCM 6 %, CBM 20 %, and DBM 74 % ) ; bromine, 539 g; AlCl3, 9 g; and ceramic beads (1.5-3.5 mm diameter), 840 g.A 55 % solution of diphenyl ethane in DCM (91.1 g, ) was dropped into the flask during 30 minutes with stirring while keeping the temperature at 21-26 0C. The reaction mixture was refluxed for 6.7 hours, and 120 ml of water was carefully added to destroy the catalyst. Bromine was bleached with sodium bisulfite solution, the aqueous phase was separated and the organic phase was washed with water and was neutralized with 20 % NaOH. The product mixture was passed through a sieve to remove the ceramic beads and the mixture was filtered, washed with water and dried. The product comprised 91.4 % decabromodiphenyl ethane and 7.8 % nonabromodiphenyl ethane. Particle size was 6.1 microns (d90).; Example 10 (comparative); Decabromodiphenyl ethane – Bromination without milling in a mixed solvent.; The procedure of Example 9 was repeated without the ceramic beads present. The product comprised 80.6 % decabromodiphenyl ethane and 18.6 % nonabromodiphenyl ethane. Particle size 22 .microns (dgo).

The chemical industry reduces the impact on the environment during synthesis Diphenyl oxide. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BROMINE COMPOUNDS LTD.; WO2008/26215; (2008); A2;,
Ether – Wikipedia,
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