Category: 22385-77-9

Adding a certain compound to certain chemical reactions, such as: 22385-77-9, name is 1-Bromo-3,5-di-tert-butylbenzene, belongs to bromides-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 22385-77-9, Application In Synthesis of 1-Bromo-3,5-di-tert-butylbenzene

An oven-dried 500 mt_ round bottom flask equipped with a magnetic stir bar and rubber septum was attached to a double manifold and cooled under vacuum. The flask was backfilled with N2, the rubber septum was removed, l-bromo-3,5-di-te/t- butylbenzene (32.4 g, 120 mmol, 3.01 equiv.) was added, and the septum replaced. The flask was then purged with N2 for 15 minutes. THF (240 ml_, [0.5 M]) was added and the flask was cool to -78 C in a dry ice/acetone bath. While stirring, nBuLi (48.2 mL, 120 mmol, 3 equiv., [2.49 M] in hexanes) was added dropwise via syringe pump over 30 minutes. PCI3 (3.5 mL, 40 mmol, 1 equiv.) was added dropwise via syringe pump over 15 minutes. After the addition was complete, the flask was warmed to 0 C in an ice/water bath and stirred for 4 hours. The flask was allowed to warm to RT, the septum was removed and the reaction was quenched by adding brine (100 mL). The reaction was poured into a separatory funnel and the product was extracted 2X with Et20 (100 mL) . The organic layer was dried over MgS04, filtered through a glass frit, and the solvent removed in vacuo. The product was purified by recrystallization from hot EtOH (200 mL), cooled under ambient conditions, then placed in a -20 C freezer overnight. Collection of the solid via filtration and washing with EtOH resulted in white crystals ( 10.6 g, 44% yield) : 1H NMR (600 MHz, CDCl3) delta 7.38 (t, J = 1.8 Hz, 3H), 7.12 (dd, J = 8.5, 1.8 Hz, 6H), 1.22 (s, 54H) ; 13C NMR ( 151 MHz, CDCl3) delta 150.6 (d, J = 6.7 Hz), 137.3 (d, J = 9.4 Hz), 128.1 (d, J = 19.3 Hz), 122.4 , 35.0 , 31.5; 31P NMR (243 MHz, CDCl3) delta -3.59; FTIR (cm 1) : 2963, 1589, 1577, 1362, 1249, 1130, 875, 710; mp = 145-147 C; HRMS (LIFDI) m/z, calculated for [C42H63P] + : 598.4667; found : 598.4688.

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-3,5-di-tert-butylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UNIVERSITY OF DELAWARE; WATSON, Donald; CINDERELLA, Andrew; VULOVIC, Bojan; (76 pag.)WO2018/64163; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 22385-77-9 name is 1-Bromo-3,5-di-tert-butylbenzene, 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. 22385-77-9

Preparation 502-(3,5-Di-tert-butylphenyl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolane Bubble nitrogen through DMF (150 mL) for about 15 min prior to adding the reagents. Then dissolve l-bromo-3,5-di-tert-butylbenzene (20.93 g, 77.74 mmol), bis(pinacolato)diboron (22.70 g, 89.40 mmol), and (Iota, – bis(diphenylphosphino)ferrocene)palladium(II) chloride (3.17 g, 3.89 mmol) in the DMF. Stir for 10 min. Add potassium acetate (22.89 g, 233.23 mmol) and bubble argon through the solution for 7 min. Heat the reaction to 85 ¡ãC with stirring for 24 h. Dilute the reaction with water (1.5 L). Collect the resulting brown precipitate by vacuum filtration and washing with water. Dissolve the residue in dichloromethane. Dry this solution over sodium sulfate, filter; collect the filtrate; and concentrate under reducedpressure. Triturate the resulting solids with hot hexanes (400 mL) and filter, washing with hexanes. Concentrate the filtrate to a volume of approximately 300 mL. Place the solution in a freezer overnight. Collect the solid by vacuum filtration and rinsing with cold hexanes. Concentrate the filtrate under reduced pressure to a volume of 150 mL. Cool this mixture in the freezer for about 1.5 h. Collect the resulting solids by vacuum filtration and rinse with cold hexanes. Combine the 2 crops and dry under high vacuum to afford the title compound (21.85 g, 89percent) as a light tan crystalline solid. XH NMR (400 MHz, CDC13) delta 1.33 (s, 12H), 1.33 (s, 18H), 7.53 (t, J = 2.0 Hz, 1H), 7.65 (d, J = 2.0 Hz, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-3,5-di-tert-butylbenzene, and friends who are interested can also refer to it.

Reference:
Patent; ELI LILLY AND COMPANY; BLEISCH, Thomas, John; COATES, David, Andrew; HUGHES, Norman, Earle; JONES, Scott, Alan; NORMAN, Bryan, Hurst; WO2013/66640; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

22385-77-9, The chemical industry reduces the impact on the environment during synthesis 22385-77-9, name is 1-Bromo-3,5-di-tert-butylbenzene, I believe this compound will play a more active role in future production and life.

Preparation 13 ,5-Di-/er/-butylbenzaldehydeDissolve l-bromo-3,5-di-/er/-butylbenzene (5.00 g, 18.57 mmol) in THF (50 mL) under a nitrogen atmosphere. Cool to -78 C. Slowly add w-butyllithium (2.5 M in hexanes) (22.29 mL, 55.72 mmol) at -78 C. Stir at -78 C for about 30 min. Add DMF (4.31 mL, 55.72 mmol) dropwise. Warm the mixture to 0 C and stir for 2.5 h. Pour aqueous NH4CI (30 mL) into the mixture. Extract with EtOAc (3 x 20 mL). Dry the combined organic portions over a2S04; filter; collect the filtrate; and concentrate under reduced pressure. Purify the residue using flash chromatography eluting with a gradient of 0-10% EtO Ac/petroleum ether to afford the title compound (2.96 g, 73%) as a white solid. LC-ES/MS m/z 219 [M+H]+.

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-3,5-di-tert-butylbenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ELI LILLY AND COMPANY; BLEISCH, Thomas, John; COATES, David, Andrew; HUGHES, Norman, Earle; JONES, Scott, Alan; NORMAN, Bryan, Hurst; WO2013/66640; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

22385-77-9, 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. 22385-77-9, name is 1-Bromo-3,5-di-tert-butylbenzene, This compound has unique chemical properties. The synthetic route is as follows.

2-methyl-4-methoxy-7-(3,5-Di-tert-butylphenyl)-1H-indene To a solution of 3,5-di-tert-butylphenylmagnesium bromide obtained from 59.3 g (0.220 mol) of 1-bromo-3,5-di-tert-butylbenzene and 7.60 g (0.313 mol, 1.42 eqv.) of magnesium turnings in 450 ml of THF 1.00 g (1.28 mmol, 0.65 mol. percent) NiCl2(PPh3)IPr and a solution of 53.4 g (0.197 mol) of 2-methyl-4-bromo-1,7-dimethoxyindane in 50 ml of THF were added. A vigorous reflux occurs approximately after ca. 30 sec and ceased after the following 30 sec. This mixture was stirred for 30 min at room temperature. Finally, 1000 ml of water and then 50 ml of 12 M HCl were added. The product was extracted with 500 ml of dichloromethane, organic layer was separated, the aqueous layer was additionally extracted with 200 ml of dichloromethane. The combined organic extract was dried over K2CO3, passed through a short column with silica gel 60 (40-63 mum), and then evaporated to dryness. To the residue dissolved in 700 ml of toluene 1.4 g of TsOH was added. This solution was refluxed using Dean-Stark head for 20 min, cooled to room temperature, washed with 200 ml of 10percent aqueous NaHCO3. The organic layer was separated, the aqueous layer was extracted with 2*100 ml of dichloromethane. The combined organic solution was evaporated to dryness. The product was isolated by flash chromatography on silica gel 60 (40-63 um; eluent: hexane-dichloromethane=10:1, then 1:1, vol.). This procedure gave 67.6 g (99percent) of 2-methyl-4-methoxy-7-(3,5-di-tert-butylphenyl)-1H-indene as a yellowish crystalline powder. The latter can be recrystallized from n-hexane with marginal loss of weight. Anal. calc. for C25H32O: C, 86.15; H, 9.25. Found: C, 86.09; H, 9.23. 1H NMR (CDCl3): delta 7.40 (m, 1H, 4-H in tBu2C6H3), 7.35 (m, 2H, 2,6-H in tBu2C6H3), 7.15 (d, J=8.4 Hz, 1H, 6-H in indenyl), 6.88 (d, J=8.4 Hz, 1H, 5-H in indenyl), 6.70 (m, 1H, 3-H in indenyl), 3.92 (s, 3H, OMe), 3.41 (m, 2H, 2,2′-H in indenyl), 2.15 (s, 3H, 2-Me in indenyl), 1.38 (s, 18H, tBu).

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; BOREALIS AG; RESCONI, Luigi; CASTRO, Pascal; VIRKKUNEN, Ville; IZMER, Vyatcheslav V.; KONONOVICH, Dmitry S.; KULYABIN, Pavel Sergeevich; VOSKOBOYNIKOV, Alexander Z.; US2015/344596; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 22385-77-9 name is 1-Bromo-3,5-di-tert-butylbenzene, 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. 22385-77-9

A solution of 2,2,6,6-tetramethylpiperidine (2.0 mL, 12 mmol) in THF (12 mL) was treated with n-BuLi (7.5mL, 1.60 M in hexane, 12 mmol) at 0 ¡ãC. After stirring for 1 h at 0 ¡ãC the solution wasadded to a solution of bromoferrocene (1.32 g, 5.00 mmol) in THF (10 mL) at ?78 ¡ãC.After stirring for 30 min at ?78 ¡ãC and 3 h at ?30 ¡ãC the reaction mixture wastransferred to a suspension of ZnCl2 (1.36 g, 10.0 mmol) in THF (10 mL) at ?78 ¡ãC.Stirring was continued at ?78 ¡ãC for 30 min before the mixture was warmed to roomtemperature, where stirring was maintained for 30 min. To the resulting solution wasadded a solution of 1-bromo-3,5-di-t-butylbenzene (1.48 g, 5.50 mmol) and [Pd(PPh3)4](0.29 g, 0.25 mmol) in THF (10 mL). The reaction mixture was heated to 60 ¡ãC for 10hours, before the reaction was quenched with a saturated aqueous ammonium chloridesolution. The reaction mixture was extracted with hexane and the combined organicphases were washed with water and dried over MgSO4. After filtration, the filtrate wasevaporated to dryness under reduced pressure and the obtained residue was purified bycolumn chromatography on silica gel (hexane) to give compound 3 (2.01 g, 4.43 mmol,89percent). 3: orange solid; m.p. 87?89 ¡ãC; 1H NMR (300 MHz, CDCl3) delta 1.37 (s, 18H), 4.17(s, 5H), 4.22 (t, J = 2.6 Hz, 1H), 4.43 (dd, J = 2.6, 1.4 Hz), 4.54 (dd, J = 2.6, 1.4 Hz),7.33 (t, J = 1.8 Hz, 1H), 7.55 (d, J = 1.8 Hz, 2H); 13C NMR (75 MHz, CDCl3) delta 31.6 (q),34.8 (q), 66.3 (d), 67.5 (d), 71.0 (d), 72.0 (d), 78.3 (s), 87.7 (s), 120.8 (d), 123.9 (d),135.2 (s), 149.8 (s). Anal. Calcd for C24H29BrFe: C, 63.60; H, 6.45percent. Found: C, 63.84;H, 6.48percent.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 22385-77-9, and friends who are interested can also refer to it.

Reference:
Article; Sasamori, Takahiro; Suzuki, Yuko; Sakagami, Michiyasu; Miyake, Hideaki; Tokitoh, Norihiro; Chemistry Letters; vol. 43; 9; (2014); p. 1464 – 1466;,
Bromide – Wikipedia,
bromide – Wiktionary

22385-77-9, name is 1-Bromo-3,5-di-tert-butylbenzene, belongs to bromides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. 22385-77-9

To a solution of 3 (1.5 g, 5.6 mmol) in anhydrous toluene (30 mL), 1-bromo-3,5-di-tert-butylbenzene (1.8 g, 6.7 mmol), was added t-BuONa, (1.2 g 13.4 mmol), and P(t-Bu)3 (1.38 mmol, 2.8 mL of a 10 wtpercent hexane solution) under argon. After stirring under reduced pressure, Pd(dba)2 (0.16 g, 0.28 mmol) was added to the solution. The reaction mixture was stirred at 110 ¡ãC for 16 h under argon. The precipitated solid was removed by filtration, and then the residue was washed with toluene (30 mL). After addition of methanol, precipitation occurred in the solution. The solid residue after filtration was washed with methanol (30 mL), and then was recrystallized from acetone to yield 6b (2.2 g, 86percent) as a pale-yellow powder. 6b: mp: 197 ¡ãC; 1H-NMR (400 MHz, CDCl3): delta = 1.40 (s, 18H, DBC-N-Ph-C(CH3)3), 7.40 (s, 2H, aromatic ring), 7.52 (dd, 2H, J = 14.8, 7.6 Hz, aromatic ring), 7.59 (dd, 3H, J = 8.8, 3.6 Hz, aromatic ring), 7.70 (dd, 2H, J = 15.2, 7.2 Hz, aromatic ring), 7.84 (d, 2H, J = 9.2 Hz, aromatic ring), 8.03 (d, 2H, J = 7.6 Hz, aromatic ring), 9.27 (d, 2H, J = 8.8 Hz, aromatic ring); 13C-NMR (75 MHz, CDCl3): delta = 31.474, 35.16, 112.04, 117.43, 122.04, 122.26, 123.35, 125.40, 126.65, 129.07, 129.11, 130.10, 136.23, 138.02, 152.77; FT-IR (nu cm-1): 3100, 3000, 2850, 1600, 1400, 1350, 1300, 1250, 900, 675; HRMS calcd. for C34H33N ([M+Na]+): 478.2505, found: 478.2506.

Statistics shows that 22385-77-9 is playing an increasingly important role. we look forward to future research findings about 1-Bromo-3,5-di-tert-butylbenzene.

Reference:
Article; Hassan, Fathy; Kawamoto, Masuki; Salikolimi, Krishnachary; Hashizume, Daisuke; Hirose, Takuji; Ito, Yoshihiro; Tetrahedron Letters; vol. 59; 2; (2018); p. 99 – 102;,
Bromide – Wikipedia,
bromide – Wiktionary

A common heterocyclic compound, 22385-77-9, name is 1-Bromo-3,5-di-tert-butylbenzene, molecular formula is C14H21Br, 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. 22385-77-9.

Compound 9 (12.2 g, 24.5 mmol) was dissolved in THF (100 mL) and cooled to -78 ¡ãC. To thissolution was added at -78 ¡ãC a freshly prepared solution of LDA from diisopropylamine (5.15 mL, 36.7mmol) and n-BuLi (22.2 mL, 1.65 M, 36.7mmol) in THF (50 mL). After stirring at -78 ¡ãC for 30 min, the resulting solution was added to asuspension of ZnCl2 (12.1 g, 89.1mmol) in THF (100 mL) at -78 ¡ãC. The reaction mixture was stirred at -78 ¡ãC for 1 h and warmed to room temperature, where stirring was continued for 1 h. The resulting solution was added to a solution of 1-bromo-3,5-di-t-butylbenzene (6.60 g, 24.5mmol) and [Pd(PPh3)4] (1.42 g, 1.22 mmol) in THF (50 mL). The resulting solution was heated at 60 ¡ãC for 10 h, before the reaction was quenched by addition of saturated aqueous sodium hydrogen carbonate. The reaction mixture was extracted with Et2O and the combined organic phases were washed with water and dried over MgSO4. After filtration and evaporation of all volatiles under reduced pressure, the obtained residue was purified by column chromatography on silica gel (hexane/ethyl acetate 1:1) to give10 (13.5 g, 19.7mmol, 80percent).

The synthetic route of 1-Bromo-3,5-di-tert-butylbenzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sakagami, Michiyasu; Sasamori, Takahiro; Sakai, Heisuke; Furukawa, Yukio; Tokitoh, Norihiro; Bulletin of the Chemical Society of Japan; vol. 86; 10; (2013); p. 1132 – 1143;,
Bromide – Wikipedia,
bromide – Wiktionary

22385-77-9, Adding some certain compound to certain chemical reactions, such as: 22385-77-9, name is 1-Bromo-3,5-di-tert-butylbenzene, 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 22385-77-9.

General procedure: To a solution of phthalimide (20 mmol) in CH2Cl2 (70 mL) was added the Grignard reagent (preformed from 50 mmol ArBr, 60 mmol mg in 30 mL THF) at room temperature. The resulting mixture was stirred at room temperature for 1.5 h and quenched with saturated aqueous solution of NH4Cl (40 mL). Then the mixture was extracted with ethyl acetate and washed with brine. The collected organic phase was dried over anhydrous Na2SO4 and concentrated under vacuum. The residue was purified by chromatography, eluting with ethyl acetate/petroleum ether 1:1 (v/v), to afford the 3-aryl-3-hydroxyisoindolin-1-ones.

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 22385-77-9.

Reference:
Article; Ge, Chen; Liang, Ren-Xiao; Liu, Ren-Rong; Xiang, Bin; Jia, Yi-Xia; Tetrahedron Letters; vol. 58; 2; (2017); p. 142 – 144;,
Bromide – Wikipedia,
bromide – Wiktionary

22385-77-9, 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 22385-77-9 as follows.

To a solution of 1-bromo-3,5-di-tert-butylbenzene (527 mg, 1.96 mmol) in Et2O (10mL) at -78 C under N2 atmosphere was added dropwise n-BuLi (1.65 M in hexane, 1.1mL, 1.82 mmol). The resulting solution was warmed to room temperature and stirredfor 1 h. This solution was added dropwise to a solution of5,15-bis(triisopropylsilylethynyl)porphyrin2 (200 mg, 298 mumol) in dry THF (10 mL).After the mixture was stirred at room temperature overnight, water (1.0 mL) and thenDDQ (204 mg, 90.0 mumol) were added. The reaction mixture was stirred for additional 20 min before addition of triethylamine (0.2 mL). The volatiles were removed in vacuoand the residue was taken up in CH2Cl2 and washed with water and brine. The organiclayer was dried over Na2SO4 and concentrated. The residue was separated by silica-gelcolumn chromatography (CH2Cl2/hexane=1/4 as an eluent). After removal of thesolvent in vacuo, recrystallization from CH2Cl2/MeOH gave 5 (195 mg, 227 mumol) in76% yield as a purple solid. 1H NMR (400 MHz, CDCl3, RT): delta = 10.06 (s, 1H,meso-H), 9.72 (d, J = 4.4 Hz, 2H, beta-H), 9.64 (d, J = 4.8 Hz, 2H, beta-H), 8.87 (d, J = 4.8Hz, 2H, beta-H), 7.99 (d, J = 1.6 Hz, 2H, Ar-o), 7.81 (t, 2H, J = 1.8 Hz, Ar-p), 1.53 (s, 18H,tBu), 1.47 (s, 18H, tBu), 1.44 (s, 18H, tBu), and -2.40 (br, 2H, NH) ppm; 13C NMR(126 MHz, CDCl3): delta = 148.8, 140.7, 129.4 (br), 129.3, 123.7, 121.4, 106.2, 100.5,99.27, 35.0, 31.7, 19.1, 12.1, and 11.8 ppm; HR-MS (ESI): m/z = 859.5579 calcd for(C56H75N4Si2)+ = 859.5525 [(M+H)+].

According to the analysis of related databases, 1-Bromo-3,5-di-tert-butylbenzene, the application of this compound in the production field has become more and more popular.

Reference:
Article; Takiguchi, Asahi; Wakita, Mana; Hiroto, Satoru; Shinokubo, Hiroshi; Chemistry Letters; vol. 48; 4; (2019); p. 371 – 373;,
Bromide – Wikipedia,
bromide – Wiktionary