Category: 454-90-0

Adding a certain compound to certain chemical reactions, such as: 454-90-0, name is 3-(Trifluoromethyl)anisole, 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 454-90-0, Quality Control of 3-(Trifluoromethyl)anisole

In each of the examples in Table 3A, the substrate is reacted with the base in THF to form a metallic organoborate intermediate under the temperature and time conditions specified in Table 3A. The metallic organoborate intermediate is then reacted with the electrophile, E, in THF to form the functionalized products 11b to 11g under the following conditions:Similarly, the substituted arenes 10b-d reacted with 2b (25 C, 0.5-12 h) affording the corresponding borate which lead after subsequent cross-coupling (ZnCl2 (10 mol%), Pd(OAc)2 (3 mol%), S-Phos (6 mol%), 65 C, 1 h) with 12 (0.8 equiv) to the biphenyl derivatives llb-d in 75-95% yield (Table 3A, entries 2-4). For example, tmpBEtyMgCl LiCl (2.2 mL, 1.0 M in THF, 2.2 mmol) was added dropwise at 25 C to a solution of 3,5-(trifluoromethyl)anisole (10b; 352 mg, 2.0 mmol) in THF (2 mL) in a flame-dried and Argon-flushed Schlenk-tube equipped with septum and magnetic stirring bar. After stirring for 1 h at 25 C, ZnCl2 (0.2 mL, 1 M in THF, 10 mol%), Pd(OAc)2 (14 mg, 3 mol%), S-Phos (25 mg, 6 mol%) and ethyl 4-iodobenzoate (12; 441 mg, 1.6 mmol) were added followed by continuously stirring for 1 h at 65 C. After cooling to 25 C, the reaction mixture was diluted with Epsilon2Omicron (5 mL) and quenched with sat. NH4C1 (aq.) (5 mL). The aqueous layer was extracted with CH2CI2 (3x 15 mL). The combined organic phases were dried over Na2SC>4 and the solvent was removed under vacuum. Flash column chromatography (pentane-Et20, 9: 1) afforded lib (492 mg, 95%) as a pale yellow 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:
Patent; HAAG, Benjamin; WO2012/85169; (2012); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 454-90-0, The chemical industry reduces the impact on the environment during synthesis 454-90-0, name is 3-(Trifluoromethyl)anisole, I believe this compound will play a more active role in future production and life.

A flame-dried 100 mL Schlenk tube was charged with bis(pinacolato)diboron (350 mg, 1.38 mmol), [Ir(COD)Cl]z (12 mg, 0.018 mmol), sodium methoxide (5 mg, 0.09 mmol), and 4,4′-di-tert-butyl-2,2′-dipyridyl (8 mg, 0.03 mmol). The flask was evacuated, placed under argon, and 3-trifluoromethylanisole (2.5 mL) was added. The flask was restoppered and evacuated (full vacuum, 2 minutes). The flask was sealed under vacuum and maintained at 90 C. (oil bath) for 96 h. Thereafter, the contents were transferred to a round bottom flask with the aid of ethyl acetate and purified by Kugelrohr distillation. The product, a viscous oil, distills at 120 C. 10 p.m. Isolated yield 497 mg (1.65 mmol, 60%). 1H NMR (400 MHz, CDCl3) delta 7.62 (s, 1H); 7.43 (s, 1H); 7.18 (s, 1H); 3.82 (s, 1H); 1.32 (s, 1H).

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-(Trifluoromethyl)anisole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; The Regents of the University of California; Tanaka, Masahiro; Zhang, Chao; Shokat, Kevan M.; Burlingame, Alma L.; Hansen, Kirk; Bateman, Raynard L.; DiMagno, Stephen G.; (81 pag.)US2016/168151; (2016); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 454-90-0, name is 3-(Trifluoromethyl)anisole, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H7F3O

1. 2-Methoxy-6-trifluoromethylthiophenol. A three-neck 125 milliliter (mL) flask was purged with N2 and then fitted with a N2 inlet, magnetic stir bar, thermometer and a septum. To the flask was added 3-trifluoromethylanisole (12.8 g, 73 mmol), tetrahydrofuran (THF; 37 mL) and di(i-propyl)-amine (DIPA; 0.2 mL, 1.4 mmol). The solution was cooled to 0 C. and then n-BuLi (28 mL of 2.5 M in hexanes, ca. 70 mmol) was added at a rate to keep the temperature at 10-15 C. The resulting slurry was cooled to 5 C. and allowed to stir for 15 minutes (min). Gas chromatography (GC) analysis (quenched into di-n-propyl disulfide (DPS)(DPS)) indicated an isomer ratio of 77:5. DIPA (0.2 mL) was added and stirring continued for 50 min. GC analysis indicated an isomer ratio of 138:1. A second 125 mL three-neck flask was purged with N2 and fitted with a N2 inlet, Tefloncanula, stir bar and a thermometer. This vessel was loaded with sulfur (2.3 g, 72 mmol) and THF (20 mL). The resulting slurry was cooled to 5 C. and then the aryl lithium slurry was added via canula at a rate to maintain the temperature at 15-20 C. After the addition was complete the resulting amber solution was stirred at 10-15 C. for 35 min. The mixture was poured into 2M HCl (50 mL) and the phases separated. The aqueous phase was extracted with ethyl acetate (EtOAc; 25 mL). The combined organic extracts were washed with brine (75 mL) and dried (MgSO4). The solvents were removed in vacuo leaving an amber oil (16.5 g): gas chromatography/mass spectrometry (GC/MS) analysis indicated the oil contained about 4 percent of the starting anisole and 2 percent of an undesired isomer of the product. 1H NMR (CDCl3): 3.93 (s, 3H), 4.54 (q, J=5 Hz, 1H), 6.99 (d, J=8 Hz, 1H), 7.16 (apparent t, J=8 Hz, 1H), 7.24 (dd, J=8Hz, 2Hz, 1H); MS (GC, 70 eV) 208 (M+, 100%), 187 (95%), 145 (80%).

The synthetic route of 454-90-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Smith, Michael Glenn; Pobanz, Mark Andrew; Roth, Gary A.; Gonzalez, Michael A.; US2002/10375; (2002); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 454-90-0, A common heterocyclic compound, 454-90-0, name is 3-(Trifluoromethyl)anisole, molecular formula is C8H7F3O, 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 stirred solution of 1-methoxy-3-(trifluoromethyl)benzene (9.8 mL, 68 mmol) in 50 mL THF under N2 at O0C was added n-BuLi (1.6 M in hexanes, 45 mL, 68 mmol) dropwise. The reaction mixture was stirred at O0C for 2 h, then triisopropylborate (11.6 ml_, 68 mmol) was added. The reaction mixture was slowly warmed up to room temperature and stirred overnight. A solution of 10% HCI in water was added and the mixture was stirred for 1 h. The mixture was extracted with CH2CI2 (3X), The organic layers were combined, washed with brine and dried over Na2SO4 to give 8.14 g of 2-methoxy-4-(trifluoromethyl)phenylboronic acid as a viscous oil. The crude was directly used in the next step without further purification.

The synthetic route of 454-90-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2008/12623; (2008); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. COA of Formula: C8H7F3O

A solution of n-butyllithium (20.4 mL, 51.1 mmol) and TMEDA (9.00 mL, 59.6 mmol) in anhydrous THF (50 mL) was cooled to -78 C. 1-Methoxy-3-(trifluoromethyl)benzene (1) (10 g, 57 mmol) was added dropwise and the reaction mixture was stirred at -78 C. for 15 min then allowed to warm to RT and stirred for 10 min. The reaction mixture was cooled to -78 C. and trimethyl borate (16.1 mL, 142 mmol) was added slowly, dropwise, and the reaction mixture was stirred at -78 C. for 15 min then allowed to warm to RT and stirred for 20 h. 7N NH3/MeOH (20 mL) was added and the solvent was removed in vacuo. The residue was dissolved in formic acid (20 mL) and cooled to 0 C. before hydrogen peroxide (6.00 mL, 68.5 mmol) was added and the solution was allowed to warm to RT and stirred for 2 h. The product was extracted with EtOAc (3*50 mL), and then the combined organics were shaken with NaOH (2*50 mL). The aq phase was acidified with 1M HCl and the product was extracted with DCM (2*30 mL). The organic solution was washed with brine (2*30 mL), dried over MgSO4 and filtered. The solvent was removed in vacuo and the residue was purified by silica gel chromatography (120 g, 0-5% MeOH in DCM) to afford 2-methoxy-6-(trifluoromethyl)phenol (2) (4.95 g, 45%) as a colourless oil: m/z 191 [M-H]- (ES-); 1H NMR (400 MHz, CDCl3) delta: 7.15-7.09 (1H, m), 7.04-6.98 (1H, m), 6.89 (1H, td), 6.14 (1H, br s), 3.91 (3H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 454-90-0, its application will become more common.

Reference:
Patent; KING’S COLLEGE LONDON; US2012/149737; (2012); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 454-90-0 name is 3-(Trifluoromethyl)anisole, 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. 454-90-0

General procedure: (b) For isolations of the major products, copper(I) chloride (0.248 g, 2.5 mmol) and Mg powder (0.486 g, 20 mmol) were stirred in DMI (20 ml, 10 ml for 7i, 7j, 7k) and TMS-Cl (5 ml, 40 mmol) for 15 min under an argon atmosphere. Then, a benzotrifluoride derivative 6 (5 mmol) was added dropwise over 5 min into the dark suspension. The solution was stirred for additional time (see Table 2), keeping the temperature 25 C (bath temperature, 50 C for 7i, 7j, 7k). After addition of 5 ml of hexane, Mg-Cu was removed by decantation and the suspension was simultaneously extracted with hexane (5 ml¡Á5). Then, the combined hexane layer was washed with 10 wt % HCl aq and brine. After drying over sodium sulfate, purification by column chromatography on silica gel (hexane eluent) and distillation afforded the product.

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

Reference:
Article; Utsumi, Shinya; Katagiri, Toshimasa; Uneyama, Kenji; Tetrahedron; vol. 68; 4; (2012); p. 1085 – 1091;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem