Category: 2051-99-2

Application of 2051-99-2, 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. 2051-99-2 name is 1-Bromo-4-isobutylbenzene, 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.

General procedure: To a 50-mL two-neck round-bottom flask equipped with a cannula were added magnesium turnings (608 mg, 25 mmol), and the flask was heated at 80 C in vacuo for 1 h. A solution of the 4-isobutylphenyl bromide (426 mg, 2.0 mmol) in THF (5 mL) was added dropwise over 3 min under argon. The mixture was heated at 50 C until the reaction was initiated. Additional 4-isobutylphenyl bromide (1.71 g, 8.0 mmol) in THF (11.6 mL) was then added slowly via cannula over 15 min. The reaction mixture was heated at reflux for 3 h, after which a solution of 4-isobutylphenyl magnesium bromide 5 was obtained. To a separate 50-mL Schlenk tube was added anhydrous CoBr2 (21.9mg, 0.10mmol), and the tube was heated at 50C in vacuo for 2h. After cooling to room temperature, the cyclopropane-based bisoxazoline ligand 2 (0.12mmol) in THF (3mL) was added under argon. The resulting mixture was stirred for 1h at the same temperature, with 2-bromopropanoate 6 (1mmol) being added via syringe. The mixture solution was cooled to -80C, and the prepared Grignard reagent 5 (2.8mL, 0.5M in THF, 1.4mmol) was then added over 1h via syringe. The reaction mixture was stirred for another 6h at -80C and then quenched with saturated NH4Cl solution (5mL). The aqueous phase was extracted with diethyl ether (4×10mL). The combined organic phases were dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (n-hexane/ethyl acetate 100:1). 4.4.8 (S)-Cyclohexylmethyl 2-(4-isobutylphenyl)propanoate 7h Colorless oil, 89% yield, 86:14 er. The enantiomeric ratio was determined by HPLC with a Daicel Chiralcel OJ-H column (0.5% 2-propanol in n-hexane, 0.5 mL/min, 220 nm, minor tr = 8.45 min (R), major tr = 9.84 min (S)). [alpha]D20 = +18.3 (c 1.1, CHCl3). 1H NMR (300 MHz, CDCl3) delta: 7.20 (d, J = 8.1 Hz, 2H), 7.08 (d, J = 8.1 Hz, 2H), 3.92-3.81 (m, 2H), 3.69 (q, J = 7.2 Hz, 1H), 2.44 (d, J = 7.2 Hz, 2H), 1.88-1.79 (m, 1H), 1.68-1.57 (m, 6H), 1.49 (d, J = 7.2 Hz, 3H), 1.25-1.06 (m, 3H), 0.89 (d, J = 6.6 Hz, 6H), 0.84-0.79 (m, 2H). 13C NMR (75 MHz, CDCl3) delta: 174.7, 140.4, 138.0, 129.2, 127.1, 69.7, 45.2, 45.0, 37.1, 30.2, 29.5, 29.46, 26.3, 25.6, 22.3, 18.3. HRMS (APCI-TOF): calcd for C20H31O2 [M+H]+ 303.2324, found 303.2329.

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

Reference:
Article; Liu, Feipeng; Bian, Qinghua; Mao, Jianyou; Gao, Zidong; Liu, Dan; Liu, Shikuo; Wang, Xueyang; Wang, Yu; Wang, Min; Zhong, Jiangchun; Tetrahedron Asymmetry; vol. 27; 14-15; (2016); p. 663 – 669;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 2051-99-2, name is 1-Bromo-4-isobutylbenzene, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 2051-99-2

Intermediate A6 2-(4-isobutylphenyl)-6-methoxy-3.4-dihvdroisoquinolin-l(2H)-one vial, 6-methoxy-3,4-dihydroisoquinolin-l(2H)-one (0.25 g, 1.411 mmol) was dissolved in N-dimethylformamide (2.82 ml). To this was added l-bromo-4-isobutylbenzene (0.451 g, 2.116 mmol) and potassium carbonate (0.390 g, 2.82 mmol). The reaction mixture was flushed with nitrogen, charged with copper(I) iodide (0.161 g, 0.847 mmol) and heated to 150 C for 24 h. The reaction mixture was cooled to room temperature, quenched with water and extracted three times with dichloromethane. The organic layers were combined, passed through a phase separator and concentrated. The crude material was purified via silica gel chromatography using 0-75% ethyl acetate in heptanes to afford the desired product (190 mg, 0.614 mmol, 43.5 % yield) as a light orange solid. NMR (400 MHz, Chloroform-d) delta 8.12 (d, J = 8.7 Hz, 1H), 7.32 – 7.27 (m, 2H), 7.24 – 7.15 (m, 2H), 6.89 (dd, J = 8.7, 2.6 Hz, 1H), 6.77 – 6.65 (m, 1H), 3.96 (dd, J = 7.0, 6.0 Hz, 2H), 3.86 (s, 3H), 3.09 (t, J = 6.4 Hz, 2H), 2.50 (d, J = 7.1 Hz, 2H), 1.90 (dh, J = 13.5, 6.8 Hz, 1H), 0.94 (d, J = 6.6 Hz, 6H). LC MS (m/z, MH+): 310.4.

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 2051-99-2.

Reference:
Patent; NOVARTIS AG; BURKS, Heather Elizabeth; KARKI, Rajeshri Ganesh; KIRBY, Christina Ann; NUNEZ, Jill; PEUKERT, Stefan; SPRINGER, Clayton; SUN, Yingchuan; THOMSEN, Noel Marie-france; WO2015/92634; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 2051-99-2, name is 1-Bromo-4-isobutylbenzene, 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. SDS of cas: 2051-99-2

General procedure: To a 50-mL two-neck round-bottom flask equipped with a cannula were added magnesium turnings (608 mg, 25 mmol), and the flask was heated at 80 C in vacuo for 1 h. A solution of the 4-isobutylphenyl bromide (426 mg, 2.0 mmol) in THF (5 mL) was added dropwise over 3 min under argon. The mixture was heated at 50 C until the reaction was initiated. Additional 4-isobutylphenyl bromide (1.71 g, 8.0 mmol) in THF (11.6 mL) was then added slowly via cannula over 15 min. The reaction mixture was heated at reflux for 3 h, after which a solution of 4-isobutylphenyl magnesium bromide 5 was obtained. To a separate 50-mL Schlenk tube was added anhydrous CoBr2 (21.9mg, 0.10mmol), and the tube was heated at 50C in vacuo for 2h. After cooling to room temperature, the cyclopropane-based bisoxazoline ligand 2 (0.12mmol) in THF (3mL) was added under argon. The resulting mixture was stirred for 1h at the same temperature, with 2-bromopropanoate 6 (1mmol) being added via syringe. The mixture solution was cooled to -80C, and the prepared Grignard reagent 5 (2.8mL, 0.5M in THF, 1.4mmol) was then added over 1h via syringe. The reaction mixture was stirred for another 6h at -80C and then quenched with saturated NH4Cl solution (5mL). The aqueous phase was extracted with diethyl ether (4×10mL). The combined organic phases were dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (n-hexane/ethyl acetate 100:1). 4.4.5 (S)-Benzyl 2-(4-isobutylphenyl)propanoate 7e Colorless oil, 93% yield, 91:9 er. The enantiomeric ratio was determined by HPLC with a Daicel Chiralcel OJ-H column (8.0% 2-propanol in n-hexane, 0.5 mL/min, 220 nm, minor tr = 16.94 min (R), major tr = 21.49 min (S)). [alpha]D20 = +76.1 (c 1.1, CHCl3). 1H NMR (300 MHz, CDCl3) delta: 7.36-7.07 (m, 9H), 5.15-5.06 (m, 2H), 3.75 (q, J = 7.2 Hz, 1H), 2.45 (d, J = 7.2 Hz, 2H), 1.89-1.80 (m, 1H), 1.51 (d, J = 7.2 Hz, 3H), 0.90 (d, J = 6.6 Hz, 6H). 13C NMR (75 MHz, CDCl3) delta: 174.5, 140.5, 137.6, 136.1, 129.3, 128.4, 127.9, 127.7, 127.2, 66.2, 45.1, 45.0, 30.2, 22.3, 18.4. HRMS (APCI-TOF): calcd for C20H25O2 [M+H]+ 297.1855, found 297.1854.

The synthetic route of 1-Bromo-4-isobutylbenzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liu, Feipeng; Bian, Qinghua; Mao, Jianyou; Gao, Zidong; Liu, Dan; Liu, Shikuo; Wang, Xueyang; Wang, Yu; Wang, Min; Zhong, Jiangchun; Tetrahedron Asymmetry; vol. 27; 14-15; (2016); p. 663 – 669;,
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. 2051-99-2, name is 1-Bromo-4-isobutylbenzene, A new synthetic method of this compound is introduced below., Recommanded Product: 1-Bromo-4-isobutylbenzene

A mixture of 5.0 g (23.5 mmol) of 1-bromo-4-isobutylbenzene, 3.14 g (26.7 mmol) of zinc cyanide, 963 mg (2.35 mmol) of dicyclohexyl-(2′,6′-dimethoxybiphenyl-2-yl)phosphane and 1.08 g (1.17 mmol) of tris(dibenzylidene-acetone)dipalladium in 230 ml of DMF/water (99:1) was heated at 120 C. under inert, oxygen-free conditions for 1 h. After cooling to RT, the mixture was diluted with approx. 1,000 ml of water and extracted three times with approx. 150 ml of ethyl acetate each time. The combined organic extracts were washed successively with water and saturated sodium chloride solution. After drying over anhydrous magnesium sulphate, the mixture was filtered and the filtrate was freed from the solvent on a rotary evaporator. The residue obtained was purified by means of filtration with suction over silica gel with cyclohexane/ethyl acetate 10:1 as the mobile phase. 3.04 g (81% of th.) of the title compound were obtained.1H-NMR (400 MHz, CDCl3, delta/ppm): 7.56 (d, 2H), 7.23 (d, 2H), 2.53 (d, 2H), 1.94-1.83 (m, 1H), 0.90 (d, 6H).GC/MS (method K, EIpos): Rt=4.05 min, m/z=159 [M]+.

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; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; US2011/301122; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 2051-99-2, 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. 2051-99-2 name is 1-Bromo-4-isobutylbenzene, 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.

General procedure: To a 50-mL two-neck round-bottom flask equipped with a cannula were added magnesium turnings (608 mg, 25 mmol), and the flask was heated at 80 C in vacuo for 1 h. A solution of the 4-isobutylphenyl bromide (426 mg, 2.0 mmol) in THF (5 mL) was added dropwise over 3 min under argon. The mixture was heated at 50 C until the reaction was initiated. Additional 4-isobutylphenyl bromide (1.71 g, 8.0 mmol) in THF (11.6 mL) was then added slowly via cannula over 15 min. The reaction mixture was heated at reflux for 3 h, after which a solution of 4-isobutylphenyl magnesium bromide 5 was obtained. To a separate 50-mL Schlenk tube was added anhydrous CoBr2 (21.9mg, 0.10mmol), and the tube was heated at 50C in vacuo for 2h. After cooling to room temperature, the cyclopropane-based bisoxazoline ligand 2 (0.12mmol) in THF (3mL) was added under argon. The resulting mixture was stirred for 1h at the same temperature, with 2-bromopropanoate 6 (1mmol) being added via syringe. The mixture solution was cooled to -80C, and the prepared Grignard reagent 5 (2.8mL, 0.5M in THF, 1.4mmol) was then added over 1h via syringe. The reaction mixture was stirred for another 6h at -80C and then quenched with saturated NH4Cl solution (5mL). The aqueous phase was extracted with diethyl ether (4¡Á10mL). The combined organic phases were dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (n-hexane/ethyl acetate 100:1). 4.4.1 (S)-Ethyl 2-(4-isobutylphenyl)propanoate 7a Colorless oil, 89% yield, 88:12 er. The enantiomeric ratio was determined by HPLC with a Daicel Chiralcel OJ-H column (0.5% 2-propanol in n-hexane, 0.5 mL/min, 220 nm, major tr = 12.80 min (S), minor tr = 14.45 min (R)). [alpha]D20 = +33.9 (c 1.1, CHCl3). 1H NMR (300 MHz, CDCl3) delta: 7.21 (d, J = 8.1 Hz, 2H), 7.09 (d, J = 8.1 Hz, 2H), 4.18-4.06 (m, 2H), 3.68 (q, J = 7.1 Hz, 1H), 2.45 (d, J = 7.2 Hz, 2H), 1.89-1.80 (m, 1H), 1.48 (d, J = 7.2 Hz, 3H), 1.21 (t, J = 7.1 Hz, 3H), 0.90 (d, J = 6.6 Hz, 6H). 13C NMR (75 MHz, CDCl3) delta: 174.7, 140.4, 137.9, 129.2, 127.1, 60.6, 45.2, 45.0, 30.1, 22.4, 18.6, 14.1. HRMS (APCI-TOF): calcd for C15H23O2 [M+H]+ 235.1698, found 235.1707.

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

Reference:
Article; Liu, Feipeng; Bian, Qinghua; Mao, Jianyou; Gao, Zidong; Liu, Dan; Liu, Shikuo; Wang, Xueyang; Wang, Yu; Wang, Min; Zhong, Jiangchun; Tetrahedron Asymmetry; vol. 27; 14-15; (2016); p. 663 – 669;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 2051-99-2, 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. 2051-99-2, name is 1-Bromo-4-isobutylbenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a 50-mL two-neck round-bottom flask equipped with a cannula were added magnesium turnings (608 mg, 25 mmol), and the flask was heated at 80 C in vacuo for 1 h. A solution of the 4-isobutylphenyl bromide (426 mg, 2.0 mmol) in THF (5 mL) was added dropwise over 3 min under argon. The mixture was heated at 50 C until the reaction was initiated. Additional 4-isobutylphenyl bromide (1.71 g, 8.0 mmol) in THF (11.6 mL) was then added slowly via cannula over 15 min. The reaction mixture was heated at reflux for 3 h, after which a solution of 4-isobutylphenyl magnesium bromide 5 was obtained. To a separate 50-mL Schlenk tube was added anhydrous CoBr2 (21.9mg, 0.10mmol), and the tube was heated at 50C in vacuo for 2h. After cooling to room temperature, the cyclopropane-based bisoxazoline ligand 2 (0.12mmol) in THF (3mL) was added under argon. The resulting mixture was stirred for 1h at the same temperature, with 2-bromopropanoate 6 (1mmol) being added via syringe. The mixture solution was cooled to -80C, and the prepared Grignard reagent 5 (2.8mL, 0.5M in THF, 1.4mmol) was then added over 1h via syringe. The reaction mixture was stirred for another 6h at -80C and then quenched with saturated NH4Cl solution (5mL). The aqueous phase was extracted with diethyl ether (4¡Á10mL). The combined organic phases were dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (n-hexane/ethyl acetate 100:1). 4.4.11 (S)-p-Tolyl-2-(4-isobutylphenyl)propanoate 7k Colorless oil, 93% yield, 87:13 er. The enantiomeric ratio was determined by HPLC with a Daicel Chiralcel OJ-H column (15% 2-propanol in n-hexane, 1 mL/min, 220 nm, minor tr = 8.37 min (R), major tr = 13.71 min (S)). [alpha]D20 = +26.4 (c 1.9, CHCl3). 1H NMR (300 MHz, CDCl3) delta 7.31-7.25 (m, 2H), 7.15-7.10 (m, 4H), 6.88-6.85 (m, 2H), 3.92 (q, J = 7.2 Hz, 1H), 2.47 (d, J = 7.2 Hz, 2H), 2.31 (s, 3H), 1.91-1.82 (m, 1H), 1.59 (d, J = 7.2 Hz, 3H), 0.91 (d, J = 6.6 Hz, 6H). 13C NMR (75 MHz, CDCl3) delta 173.4, 148.7, 140.7, 137.4, 135.3, 129.8, 129.5, 127.2, 121.0, 45.3, 45.1, 30.2, 22.4, 20.8, 18.6. HRMS (APCI-TOF): calcd for C20H25O2 [M+H]+ 297.1849, found 297.1842.

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, 1-Bromo-4-isobutylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Liu, Feipeng; Bian, Qinghua; Mao, Jianyou; Gao, Zidong; Liu, Dan; Liu, Shikuo; Wang, Xueyang; Wang, Yu; Wang, Min; Zhong, Jiangchun; Tetrahedron Asymmetry; vol. 27; 14-15; (2016); p. 663 – 669;,
Bromide – Wikipedia,
bromide – Wiktionary