Category: 22385-77-9

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

2,6-Bis(aniline)pyridine (500 mg, 1.914 mmol), 3,5-di-t-butyl-bromobenzene (1.26 g, 4.688 mmol), Pd2(dba)3 (87.6 mg, 95.7 mumol), BINAP (128.7 mg, 229.5 mumol) and sodium t-butoxide (552 mg, 5.744 mmol) were dissolved in 15 mL of toluene. The mixture was stirred for 48 h at 90 0C before cooling it to room temperature and quenching the reaction with 20 mL of water. After separation with dichloromethane, the volatiles were removed in vacuo from the organic extract. The obtained orange oil was passed through a silica gel column by a 20:1 mixture of dichloromethane and ethyl acetate and then was triturated from cold methanol and collected by filtration. 854 mg of pale-yellow solid 6a were obtained after a single wash (70 percent yield). 1H NMR (CDCl3) delta: 1.22 (s, 36eta, C(CH3)3), 6.93 (td, 2eta), 6.99 (t, 2H tBu-Ph-H), 7.05 (d, 4eta, tBu-Ph-H), 7.30 (td, 2eta), 7.54 (dd, 2H), 7.66 (d, 4H, Ph-H, Py-H), 7.90 (t, 1eta, Py-H), 9.8 (s, 2eta,NH). 1H-NMR (C6D6) delta: 1.22 (s, 36H, C(CH3)3), 6.86 (td, 2eta, Ph-H), 7.14 (t, 2eta), 7.1-7.2 (d+t, 3H, Py-H), 7.24 (td, 2eta, Ph-H), 7.32 (d, 4eta), 7.52 (dd, 2H, Ph-H), 7.85 (dd, 2eta, Ph-H), 10.14 (s, 2eta,NH). 13C NMR (CDCl3) delta: 31.6 (CH3), 35.0 (C(CH3)3), 114.6, 115.8, 116.1, 118.9, 120.5, 124.7, 130.0, 130.5, 138.5, 141.5, 143.2, 151.9, 157.3.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-3,5-di-tert-butylbenzene, its application will become more common.

Reference:
Patent; CALIFORNIA INSTITUTE OF TECHNOLOGY; AGAPIE, Theodor; GOLISZ, Suzanne; TOFAN, Daniel; BERCAW, John, E.; WO2008/36882; (2008); A1;,
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

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. Recommanded Product: 1-Bromo-3,5-di-tert-butylbenzene

General procedure: An oven-dried Schlenk tube with the presence of magnetic stir bar which is Teflon-coated was charged with Pd(dba)2 (11.5 mg, 0.02 mmol, 2 molpercent) and ligand L4 (8.4 mg, 0.02 mmol, 2 molpercent). The flask was evacuated and backfilled with nitrogen (3 cycles). Pre-complexation of palladium and ligand was initiated by injecting freshly distilled dry dichloromethane (2.0 mL) and Et3N (0.1 mL) into the tube. The solution was stirred and warmed with hair drier till the solvent condensed on the tube wall. The solvent was removed under vacuum. Aryl bromide (1.0 mmol), KOt-Bu (0.25 mmol), and potassium hexacyanoferrate(II) trihydrate (0.23 mmol) were charged successively to the tube followed by another 3 evacuation-nitrogen refill cycles. Water (1.0 mL) and acetonitrile (1.0 mL) were used as a solvent mixture. The tube was immersed into a preheated 50 °C oil bath for 24 hours. The reaction was quenched by cooling to ambient temperature and added with EtOAc and water. The organic supernatant was analyzed by GC. The organic layer was separated and the remained aqua medium was further extracted with EtOAc (10 mL .x. 3). The combined organic phases were concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel (230-400 mesh). The pure fractions were collected, dried under vacuum, and followed by proton (1H) and carbon (13C) NMR characterization

According to the analysis of related databases, 22385-77-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Yeung, Pui Yee; Tsang, Chun Pui; Kwong, Fuk Yee; Tetrahedron Letters; vol. 52; 52; (2011); p. 7038 – 7041;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 22385-77-9, name is 1-Bromo-3,5-di-tert-butylbenzene, 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. Recommanded Product: 22385-77-9

A solution of diisopropylamine (8.33 mL,59.5mmol) in THF (20 mL) was treated with n-BuLi (36.1 mL,1.65M in hexane, 59.5 mmol), and the resulting solution of lithium diisopropylamide (LDA) was added to a solution of ferrocenyl phenyl sulfoxide (6) (12.3 g, 39.7mmol) in THF (100 mL) at -78 °C. After stirring at -78 °C for 30 min, the resulting solution was transferred to a suspension of ZnCl2 (16.2 g, 119 mmol) in THF (100 mL) at -78 °C. After stirring at -78 °C for 1 h, the reaction mixture was warmed to room temperature, where stirring was maintained for 1 h. The resulting solution was added to a solution of 1-bromo-3,5-di-t-butylbenzene (10.7 g, 39.7mmol) and [Pd(PPh3)4] (2.30 g, 1.99 mmol) in THF (50 mL). The reaction mixture was heated at 60 °C for 10 h, and then the reaction was quenched with a saturated aqueous sodium hydrogen carbonate solution. The reaction mixture was extracted with Et2O, and the combined organic phases were washed with water and dried over MgSO4. After filtration, the filtrate was evaporated to remove the solvent under reduced pressure. The obtained residue was purified by column chromatography on silica gel (hexane/ethylacetate 1:1) to give 7 (16.8 g, 33.7mmol, 85percent).

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

Electric Literature of 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.

In a 500mL dry three-necked bottle, Compound 9 (23.8 g, 0.1 mol) was first dissolved in 200 mL of dry tetrahydrofuran. The flask was placed at -10 ° C. Compound 10 was slowly added (26.9 g, 0.1 mol) And t-BuLi (60 mL, 1 M in THF, 60 mmol), The reaction was carried out for 20 h under a nitrogen atmosphere. After the reaction, water is added to quench the reaction. Then with ethyl acetate, Water extraction reaction, Dry over anhydrous sodium sulfate, Concentrated under reduced pressure, Further column chromatography gave Compound 8 (21 g, 50percent).

According to the analysis of related databases, 22385-77-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wanhua Chemical Group Co., Ltd.; Wang Zesheng; Cong Xin; He Guangwen; Liu Chao; Dong Ke; Wang Peng; Cui Qian; Yu Yanbing; (12 pag.)CN109134538; (2019); A;,
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. COA of Formula: C14H21Br

Bromo-3,5-di-tert-butylbenzene (1.3 g, 5 mmole) was dissolved in THF (20 mL), to this solution was slowly added n-BuLi (1.6 M, 3.3 mL) at -78° C., the reaction was stirred at this temperature for 30 min, trimethyl borate (0.75 g, 7.5 mmole) was added all at once, stir over night while the reaction was allowed to slowly warm up to room temperature. Hydrochloric acid (6N, 5 mL) was added and stirred for 3 hrs at room temperature. Water (200 mL) was added, and the precipitate was collected, washed with water (10 mL.x.3), dried under vacuum to give titled compound.

The synthetic route of 22385-77-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Adams, Alan D.; Santini, Conrad; US2009/30012; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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, Formula: C14H21Br

General procedure: To a mixture of Pd(OAc)2 (23 mg, 0.1 mmol), DPE-Phos (125 mg,0.2 mmol), and Cs2CO3 (652 mg, 2.0 mmol) was added a solutionof 4a (496 mg, 1.0 mmol) and 2-bromo-1,3,5-trimethylbenzene(300 mg, 1.5 mmol) in 1,4-dioxane (15 mL) under N2, and the reactionmixture was heated at 110 °C for 17 h with stirring. After coolingto r.t., and removal of solvents, the mixture was extracted withCH2Cl2 (3 × 20 mL), and the combined organic extracts werewashed with brine (20 mL) and dried (Na2SO4). Purification of theresidual oil by column chromatography on silica gel (hexanes?EtOAc, 10:1) afforded 5a

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:
Article; Zhu, Shifa; Wang, Chao; Zhao, Songxian; Xiao, Yelin; Hu, Lang; Huang, Zhipeng; Synthesis; vol. 46; 2; (2014); p. 212 – 224;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 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.

5.8 g (238.6 mmol) of magnesium turnings are initially introduced into a flask which has been dried by heating, and a solution of 73 g (271.1 mmol) of bromo-3,5-d-tert-butylbenzene in 400 ml of dry THF is slowly added dropwise so that the reaction solution constantly boils under reflux. When the addition is complete, the solution is heated under reflux for a further 2 h and then allowed to cool. 20 g (108.5 mmol) of cyanogen chloride in 400 ml of dry THF are initially introduced in a further flask and cooled to 0 C. The Grignard reagent is added dropwise at such a rate that an internal temperature of 20 C. is not exceeded. When the addition is complete, the reaction mixture is warmed at room temperature overnight. The reaction is stopped by addition of 500 ml of 1 N HCl solution with ice-cooling. The phases are separated, and the aqueous phase is rinsed a number of times with ethyl acetate. The organic phases are combined and dried using saturated NaCl solution, and the solvent is then removed in vacuo. Methanol is added to the pale-brown oil, and the mixture is heated under reflux. After cooling, the solid is filtered off with suction, washed with heptane and dried in vacuo, giving 23.6 g (48.0 mmol, 44% yield) of a colourless solid.

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; MERCK PATENT GMBH; Koenen, Nils; Stoessel, Philipp; Hayer, Anna; Heil, Holger; Harbach, Philipp; (236 pag.)US9853228; (2017); B2;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 22385-77-9, name is 1-Bromo-3,5-di-tert-butylbenzene, 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. Safety of 1-Bromo-3,5-di-tert-butylbenzene

Production Example 2 of Optically Active AminoalcoholA 200 mL round-bottom four-neck flask equipped with a Dimroth condenser with a nitrogen introducing tube attached thereto, a thermometer, a magnetic rotator and a dropping funnel was heated under reduced pressure, nitrogen was then introduced into the flask, pressure in the flask was returned to normal pressure, and the flask was cooled to room temperature. After 1.27 g of magnesium and a minor amount of iodine were added to the flask, a small amount of a solution obtained by mixing 15.00 g of 3,5-di-tert-butylbromobenzene and 75.0 mL of dehydrated tetrahydrofuran was added dropwise. The flask was heated, and it was confirmed that the Grignard reaction was initiated. Thereafter, the remaining solution was added dropwise to the flask over 30 minutes. The resulting mixture was refluxed for 1.5 hours. After the resulting reaction mixture was cooled to -10° C., 1.11 g of L-valine methyl ester hydrochloride was added. After the temperature of the resulting mixture was raised to room temperature, the mixture was further refluxed for 4 hours. The resulting reaction mixture was cooled to 0 to 5° C. To the reaction solution were added dropwise 45.0 mL of an aqueous saturated ammonium chloride solution, and further 15.0 mL of water. The resulting mixture was stirred at 20° C. for 30 minutes. The resulting mixture was extracted with 45.0 mL of diethyl ether three times. The resulting organic layers were mixed, and dried with anhydrous sodium sulfate. After sodium sulfate was removed by filtration, the resulting filtrate was concentrated. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=2/9840/60) to obtain 1.02 g of a colorless crystal of (S)-2-amino-1,1-di(3,5-di-tert-butylphenyl)-3-methyl-1-butanol.1H-NMR (300 MHz, CDCl3, TMS standard)delta (ppm): 7.54 (2H, d), 7.43 (2H, d), 7.28 to 7.24 (2H, m), 4.23 (1H, brs), 3.80 (1H, d), 1.77 (1H, m), 1.35 (18H, s), 1.33 (18H, s), 1.32 (2H, s), 0.96 (3H, d), 0.87 (3H, d)13C-NMR (75 MHz, CDCl3, TMS standard)delta (ppm): 150.86, 150.43, 147.46, 144.67, 121.01, 120.80, 120.76, 120.38, 81.24, 62.12, 35.67, 35.61, 32.33, 32.27, 28.60, 23.88, 17.09

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

Reference:
Patent; Masumoto, Katsuhisa; Yoshikawa, Kouji; US2011/166372; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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

The bromide (2.0 g, 7.4 mmol), tri-nbutyi-1-ethoxyvinyl tin (3.2 g, 8.9 mmol), and PdCl2(Ph3P)2 ( 522 mg, 0.74 mmol) were dissolved in toluene 3.7 mL and the solution stirred at 95 0C for 3 hours. The volatiles were removed in vac. and the residue dissolved in 1,4-dioxane (33 mL). Aqueous HCl (2 N, 1 1 mL) was added and the solution stirred rapidly at RT for 1 hour. The mixture was diluted with water (350 mL), followed by aqueous/EtOAc work-up and silica gel chromatography (diethyl ether: hexanes (1 :9)) to give the titled compound.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-3,5-di-tert-butylbenzene, its application will become more common.

Reference:
Patent; MERCK & CO., INC.; WO2007/64553; (2007); A2;,
Bromide – Wikipedia,
bromide – Wiktionary