Category: 66417-30-9

Application of 66417-30-9, These common heterocyclic compound, 66417-30-9, name is 2-Bromo-1-methyl-4-(trifluoromethyl)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.

A solution of 2-bromo-1-methyl-4-(trifluoromethyl)benzene (4.78 g, 20 mmol) in 100 mL of anhydrous THF was cooled to -100 C (liquid nitrogen/ EtOH) under nitrogen. Then 1.4M solution of sec-BuLi in cyclohexane (15 mL, 21 mmol) was added dropwise at – 100 C to -90 C. The mixture was stirred at -100 C to -90 C for 10 min, then a solution of R-(+)-propylene oxide (1.51 g, 1.8 mL, 26 mmol) in 15 mL of THF was added dropwise at -100 C to -90 C, then the mixture was cooled to -105 C and a 46.5% solution Of BF3 in diethyl ether (4.18 mL, 30 mmol) was added dropwise. The mixture was stirred at -100 C to -90 C for 2 h, then the reaction was quenched with 20 mL of sat. aq. NH4Cl at -90 C. The mixture was stirred and warmed to 0 C overnight. Then 20 mL of water was added and mixture was extracted with EtOAc (2×60 mL), the extract was dried over Na2SO4 and evaporated to give crude oil, which was purified by column (silicagel, EtOAc/hexane 1 :9, Rf = 0.45 in EtOAc/hexane 3:7) to give (2R)-1-[2- methyl-5-(trifluoromethyl)phenyl]propan-2-ol (2.87 g, 66 %) as white solid. 1H NMR (300 MHz, CDCl3): delta 7.42 (s, 1H), 7.39 (d, J = 8.1 Hz, 1H), 7.27 (d, J = 8.1 Hz, 1H), 4.06 (m, 1H), 2.81 (d, J = 6.39 Hz, 2H), 2.39 (s, 3H), 1.43 (d, J = 4.14 Hz, 1H), 1.29 (d, J = 6.21 Hz, 3H).

The synthetic route of 66417-30-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHEMBRIDGE CORPORATION; WO2009/117097; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 66417-30-9, name is 2-Bromo-1-methyl-4-(trifluoromethyl)benzene, A new synthetic method of this compound is introduced below., Safety of 2-Bromo-1-methyl-4-(trifluoromethyl)benzene

A mixture of 2-bromo-1-methyl-4-(trifluoromethyl)benzene (5.5 g, 23.0 mmol, CAS RN 128-08-5), benzoyl peroxide (835 mg, 3.45 mmol) and NBS (4.07 g, 23.01 mmol) in CC4 (50.0 mL,23.0 mmol) was stirred at 70 C for 5 h. The mixture was poured into water (20 mL) andextracted twice with DCM (20 mL each). The combined organic layer was washed with brine(20 mL), dried over Na2SO4, filtered and concentrated in vacuum to give the desired compoundas light yellow oil which was used in the next step without further purification (7.1 g, 97%).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; ANSELM, Lilli; BENZ, Joerg; GRETHER, Uwe; GROEBKE ZBINDEN, Katrin; HEER, Dominik; HORNSPERGER, Benoit; KROLL, Carsten; KUHN, Bernd; O`HARA, Fionn; RICHTER, Hans; (268 pag.)WO2020/35425; (2020); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 66417-30-9, name is 2-Bromo-1-methyl-4-(trifluoromethyl)benzene, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Bromo-1-methyl-4-(trifluoromethyl)benzene

(a) 2-Bromo-4-(trifluoromethyl)benzoic acid. To a solution of 2-bromo-1-methyl-4-trifluoromethylbenzene (7.6 g, 32 mmol, ABCR) in pyridine (75 mL) was added tetraethylammonium permanganate (24 g, 96 mmol, prepared according to the procedure of Sala, et al. J. Chem. Soc., Chem. Comm. 1978, 253). The reaction mixture was warmed to 70 C. and stirred at that temperature for 30 h. The reaction mixture was allowed to cool to 25 C. and poured into an ice bath containing cond HCl (150 mL) and NaHSO3 (150 g). The mixture turned to a clear aqueous solution and was extracted with EtOAc (4*200 mL). The combined extracts were washed with satd NaCl (200 mL), dried over Na2SO4, filtered and concentrated in vacuo to provide the title product as a white solid. MS (ESI, neg. ion) m/z: 267 (M-1).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Bo, Yunxin Y.; Chakrabarti, Partha P.; Chen, Ning; Doherty, Elizabeth M.; Fotsch, Christopher H.; Han, Nianhe; Kelly, Michael G.; Liu, Qingyian; Norman, Mark Henry; Ognyanov, Vassil I.; Wang, Xianghong; Zhu, Jiawang; US2003/195201; (2003); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 66417-30-9, 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. 66417-30-9 name is 2-Bromo-1-methyl-4-(trifluoromethyl)benzene, 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.

Butyl lithium (1.6 M in hexane, 2.6 mL, 4.18 mmol) was added dropwise to a solution of 2-methyl-5-(trifluoromethyl)bromobenzene (1 g, 4.18 mmol) in Et2O (15 mL) at -78 C. The r.m. was stirred at -78 C. for 20 min and then 1-(tert-butyldimethylsilyloxy)-2-propanone (0.827 g, 4.39 mmol) in Et2O (5 mL) was added and the r.m. was further stirred for 2 h at -78 C. The r.m. was then quenched with water and the product was extracted with EtOAc. The organic layer was dried over MgSO4, filtered and the solvent was removed in vacuo. The crude product was purified by flash column chromatography (silica; heptanes/EtOAc 100/0 to 90/10). The fractions containing the product were collected and concentrated in vacuo to give intermediate 46 (1.036 g, 71%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-1-methyl-4-(trifluoromethyl)benzene, and friends who are interested can also refer to it.

Reference:
Patent; Janssen Pharmaceutica NV; Bischoff, Francois Paul; Velter, Adriana Ingrid; Rombouts, Frederik Jan, Rita; De Cleyn, Michel Anna, Jozef; Van Brandt, Sven Franciscus, Anna; Gijsen, Henricus Jacobus, Maria; Zavattaro, Chiara; Van den Keybus, Frans Alfons, Maria; (91 pag.)US2018/319797; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 66417-30-9, The chemical industry reduces the impact on the environment during synthesis 66417-30-9, name is 2-Bromo-1-methyl-4-(trifluoromethyl)benzene, I believe this compound will play a more active role in future production and life.

[00155] A mixture of 2-bromo-4-trifluoromethyl toluene (1 equivalent), n- butyl vinyl ether (5 equivalents), palladium acetate (0.1 equivalents), DPPP (0.22 equivalents), K2CO3 (1.2 equivalents), and DMF-H20 (0.3 M to bromide) was stirred under N2 for 18 hours at 100C. The reaction mixture was then cooled to room temperature and hydrolyzed with 5% HCI for 30 min. Extraction with EtOAc, washing with H20, sat aq. NaCi, drying (MGS04), and concentration gave an oil. Purification of the crude material by silica gel flash chromatography using an 0% hexanes to 50% HEXANES-ETOAC gradient gave 2′-methyl-5′- trifluoromethylacetophenone : the compound prepared showed a molecular ion M-= 201. 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, 2-Bromo-1-methyl-4-(trifluoromethyl)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CYTOKINETICS, INC.; WO2005/5382; (2005); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 66417-30-9, These common heterocyclic compound, 66417-30-9, name is 2-Bromo-1-methyl-4-(trifluoromethyl)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.

A solution of 2-bromo-1-methyl-4-(trifluoromethyl)benzene (4.78 g, 20 mmol) in 100 mL of anhydrous THF was cooled to -100 C (liquid nitrogen/ EtOH) under nitrogen. Then 1.4M solution of sec-BuLi in cyclohexane (15 mL, 21 mmol) was added dropwise at – 100 C to -90 C. The mixture was stirred at -100 C to -90 C for 10 min, then a solution of R-(+)-propylene oxide (1.51 g, 1.8 mL, 26 mmol) in 15 mL of THF was added dropwise at -100 C to -90 C, then the mixture was cooled to -105 C and a 46.5% solution Of BF3 in diethyl ether (4.18 mL, 30 mmol) was added dropwise. The mixture was stirred at -100 C to -90 C for 2 h, then the reaction was quenched with 20 mL of sat. aq. NH4Cl at -90 C. The mixture was stirred and warmed to 0 C overnight. Then 20 mL of water was added and mixture was extracted with EtOAc (2×60 mL), the extract was dried over Na2SO4 and evaporated to give crude oil, which was purified by column (silicagel, EtOAc/hexane 1 :9, Rf = 0.45 in EtOAc/hexane 3:7) to give (2R)-1-[2- methyl-5-(trifluoromethyl)phenyl]propan-2-ol (2.87 g, 66 %) as white solid. 1H NMR (300 MHz, CDCl3): delta 7.42 (s, 1H), 7.39 (d, J = 8.1 Hz, 1H), 7.27 (d, J = 8.1 Hz, 1H), 4.06 (m, 1H), 2.81 (d, J = 6.39 Hz, 2H), 2.39 (s, 3H), 1.43 (d, J = 4.14 Hz, 1H), 1.29 (d, J = 6.21 Hz, 3H).

The synthetic route of 66417-30-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHEMBRIDGE CORPORATION; WO2009/117097; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 66417-30-9, name is 2-Bromo-1-methyl-4-(trifluoromethyl)benzene, A new synthetic method of this compound is introduced below., Product Details of 66417-30-9

Butyl lithium (1.6 M in hexane, 2.6 mL, 4.18 mmol) was added dropwise to a solution of 2-methyl-5-(trifluoromethyl)bromobenzene (1 g, 4.18 mmol) in Et20 (15 mL) at -78 C. The r.m. was stirred at -78 C for 20 min and then l-(tert-butyldimethylsilyloxy)-2- propanone (0.827 g, 4.39 mmol) in Et20 (5 mL) was added and the r.m. was further stirred for 2 h at -78 C. The r.m. was then quenched with water and the product was extracted with EtOAc. The organic layer was dried over MgS04, filtered and the solvent was removed in vacuo. The crude product was purified by flash column chromatography (silica; heptanes/EtOAc 100/0 to 90/10). The fractions containing the product were collected and concentrated in vacuo to give intermediate 46 (1.036 g, 71%).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BISCHOFF, Francois, Paul; VELTER, Adriana, Ingrid; ROMBOUTS, Frederik, Jan, Rita; DE CLEYN, Michel, Anna, Jozef; VAN BRANDT, Sven, Franciscus, Anna; GIJSEN, Henricus, Jacobus, Maria; ZAVATTARO, Chiara; VAN DEN KEYBUS, Frans, Alfons, Maria; WO2014/111457; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 66417-30-9, 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. 66417-30-9 name is 2-Bromo-1-methyl-4-(trifluoromethyl)benzene, 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.

2-Bromo-4- (trifluoromethyl) toluene (23b, 5g, 21 mmol) was placed in round-bottom flask and dissolved in 150 ml DMF.Then KOAc (6.2g, 63 mmol, 3eq) was added to the reaction mixture in one portion followed by addition of PdCl2 (dppf)(0.46g, 0.63 mmol, 0.03eq) and Bis (pinacolato) diboron 5.9g,23.1 mmol, l.leq). The solution was stirred at 80C for 48h. Then the solvent was removed and the black residue was subjected to plug column chromatography (EtOAc) resulting in dark green oily residue. The compound was further purified by second column chromatography (2% MeOH/DCM) .Pure product (3.5g, 58%) as a slightly green oil was collected.Structure determination:RP-HPLC Conditions: HP 1100 HPLC chromatograph, Waters 3.9 x 150 mm NovaPak HR C18 column with guard column, 0.010 mL injection, 1.5 mL/min, 1.500 mL injection loop, 254 nm detection, A = water (0.1% v/v TFA) and B = MeCN (0.1% v/v TFA), gradient 10% B 1 min, 10-80% B over 9 min, 80-100% B over 1 min, 100 %B 1 min, retention time 7.9 min (for boronic acid) and 12.6 min (for pinacol ester). 1H NMR (400 MHz, CDCl3): delta 1.35 (s, 12H), 2.58 (s, 3H), 7.26 (d, IH), 7.55 (d, IH), 8.00 (s, IH).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-1-methyl-4-(trifluoromethyl)benzene, and friends who are interested can also refer to it.

Reference:
Patent; SENSORS FOR MEDICINE AND SCIENCE, INC.; WO2008/66921; (2008); A2;,
Bromide – Wikipedia,
bromide – Wiktionary